{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-2658d2fffcce43018f8455223d2c38f6","dataset_id":"ord_dataset-feaf1b793c6d408aaec1cac7cc3ceadc","reaction_class":"Minisci alkylation","transformation_sha256":"a85d2b4cac5c10575833798a4516cde536eff4f83ed99f4f661a9dc612b5c5bf","doi":"10.1021/jo9010624","dataset_source_slug":"ord-dataset-feaf1b793c6d408aaec1cac7cc3ceadc","publication_source_slug":"ord-publication-91c8bf15879e5ce2","route_slugs":["ord-2658d2fffcce43018f8455223d2c38f6-317ea33754bd","ord-2658d2fffcce43018f8455223d2c38f6-026c7b4a46c6"],"reactant_slugs":["ord-compound-986fa26b8f4ef8507bf1","ord-compound-7a5ea1f0381bb40c0ab8"],"product_slugs":["ord-compound-17a55a5f7e1abf1555e3"],"selection_notes":["Only explicitly marked REACTANT inputs become graph starting points.","Only products with a positive reported numeric YIELD become graph destinations; all reported outcomes remain in raw.","One representative record per exact reactant/product structure set; other conditions are not additional transformations."],"raw":{"identifiers":[{"type":"CUSTOM","details":"rxn_id from SURF table","value":"lsf_lit_minisci_120"},{"type":"CUSTOM","details":"rxn_tech from SURF table","value":"alkylation"},{"type":"REACTION_TYPE","details":"alkylation minisci","value":"alkylation minisci"}],"inputs":{"additive_1":{"components":[{"identifiers":[{"type":"SMILES","value":"O=S(=O)(O)O"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"7664-93-9"}],"amount":{"moles":{"value":2,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"startingmat_2":{"components":[{"identifiers":[{"type":"SMILES","value":"IC1COC1"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"26272-85-5"}],"amount":{"moles":{"value":2,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"startingmat_1":{"components":[{"identifiers":[{"type":"SMILES","value":"O=C(OCC)C=1C=CN=CC1"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"1570-45-2"}],"amount":{"moles":{"value":1,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"catalyst_1":{"components":[{"identifiers":[{"type":"SMILES","value":"[Fe].O=S(=O)(O)O.O"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"7782-63-0"}],"amount":{"moles":{"value":0.6,"units":"MILLIMOLE"}},"reaction_role":"CATALYST"}]},"reagent_1":{"components":[{"identifiers":[{"type":"SMILES","value":"OO"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"7722-84-1"}],"amount":{"moles":{"value":6,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"solvent_2":{"components":[{"identifiers":[{"type":"SMILES","value":"O"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"7732-18-5"}],"amount":{"volume":{"value":0.6,"units":"MILLILITER"}},"reaction_role":"SOLVENT"}]},"solvent_1":{"components":[{"identifiers":[{"type":"SMILES","value":"O=S(C)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"67-68-5"}],"amount":{"volume":{"value":9.4,"units":"MILLILITER"}},"reaction_role":"SOLVENT"}]}},"conditions":{"temperature":{"setpoint":{"value":40,"units":"CELSIUS"}},"pressure":{"control":{"type":"SEALED"},"atmosphere":{"type":"AIR"}}},"notes":{"procedure_details":"H2O2  (30%  in  H2O;  0.31  mL,  3.0  mmol)  was  added  dropwise  over 2 min to a stirred solution of ethyl isonicotinate 1d (151 mg, 1.0 mmol), concentrated H2SO4 (107 μL, 2.0 mmol), 3-iodooxetane (368 mg, 2.0 mmol) and iron(II) sulfate heptahydrate (80 mg, 0.3 mmol) in DMSO (10 mL) at 40 °C. After 1-2 min a further portion of iron(II) sulfate heptahydrate (80 mg, 0.3 mmol) was added and the mixture was stirred at 40 °C for 30 min. Further H2O2 (0.31 mL, 3.0 mmol) and iron(II) sulfate heptahydrate (80 mg, 0.3 mmol) was added, and the mixture was stirred at 40 °C for 60 min, then diluted with EtOAc (50 mL). The mixture was poured in to saturated NaHCO3 (5 mL) and brine (100 mL). The aqueous and organic layers were partitioned and the organic layer was washed with brine (3 x 20 mL), dried (MgSO4), filtered and the solvent removed under vacuum to leave a crude oil. The  oil  was  purified  by  column  chromatography  on  silica  gel  using  EtOAc  /  hexanes  (1:19  to  2:3)  to  give the desired product 2d (49 mg, 24%) as an oil."},"outcomes":[{"reaction_time":{"value":1.5,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"O=C(OCC)C=1C=CN=C(C1)C2COC2"},{"type":"CAS_NUMBER","value":"1180653-60-4"}],"measurements":[{"analysis_key":"MS of product_1","type":"IDENTITY"},{"analysis_key":"NMR of product_1","type":"IDENTITY"},{"analysis_key":"product_1_isolated","type":"YIELD","percentage":{"value":24}}],"reaction_role":"PRODUCT"}],"analyses":{"NMR of product_1":{"type":"NMR_1H","data":{"peaks":{"string_value":"1H NMR (400 MHz; CDCl3) δ 8.80 (d, J = 5.0 Hz,  - 6 -1H), 7.82 (s, 1H), 7.76 (dd, J = 5.0, 1.5 Hz, 1H), 5.09 (dd, J = 8.4, 5.9 Hz, 2H), 4.98 (app. t, J = 6.2 Hz, 2H),  4.47  (tt,  J  =  8.4,  6.7  Hz,  1H),  4.43  (q,  J  =  7.1  Hz,  2H),  1.43  (t, J  =  7.1  Hz,  3H);  13C  NMR  (100  MHz;  CDCl3) δ  165.1,  161.6,  150.6,  138.4,  121.2,  120.9,  76.8,  61.9,  41.8,  14.2;"}}},"product_1_isolated":{"type":"WEIGHT","details":"isolated"},"MS of product_1":{"type":"MS","details":"208.09","data":{"found":{"float_value":208.09,"description":"Observed m/z"}}}}}],"provenance":{"doi":"10.1021/jo9010624"}}},"entities":[{"slug":"ord-compound-986fa26b8f4ef8507bf1","name":"C8H9NO2 · ORD MCRPKBUFXAKDKI-UHFFFAOYSA-N","smiles":"CCOC(=O)c1ccncc1","inchi":"InChI=1S/C8H9NO2/c1-2-11-8(10)7-3-5-9-6-4-7/h3-6H,2H2,1H3","formula":"C8H9NO2"},{"slug":"ord-compound-7a5ea1f0381bb40c0ab8","name":"C3H5IO · ORD KBEIFKMKVCDETC-UHFFFAOYSA-N","smiles":"IC1COC1","inchi":"InChI=1S/C3H5IO/c4-3-1-5-2-3/h3H,1-2H2","formula":"C3H5IO"},{"slug":"ord-compound-17a55a5f7e1abf1555e3","name":"C11H13NO3 · ORD PHTCPCSTKJJVJF-UHFFFAOYSA-N","smiles":"CCOC(=O)c1ccnc(C2COC2)c1","inchi":"InChI=1S/C11H13NO3/c1-2-15-11(13)8-3-4-12-10(5-8)9-6-14-7-9/h3-5,9H,2,6-7H2,1H3","formula":"C11H13NO3"}],"dataset":{"dataset_id":"ord_dataset-feaf1b793c6d408aaec1cac7cc3ceadc","name":"Minisci dataset from Roche","description":"Minisci reactions which were extracted from the literature by Roche scientists and published in the SURF format (ChemRxiv, 2024, DOI: 10.26434/chemrxiv-2023-nfq7h)","records_in_source":130,"path":"data/fe/ord_dataset-feaf1b793c6d408aaec1cac7cc3ceadc.parquet","sha256":"ebefbe9aba687f182d4f068e94be0f7fd71d1189bdb2eff2aca6fedf4d522bf3","bytes":37643,"repository_url":"https://github.com/open-reaction-database/ord-data/blob/83f971f586f6ad18f358ae4ae99d045e94ed2066/data/fe/ord_dataset-feaf1b793c6d408aaec1cac7cc3ceadc.parquet","download_url":"https://huggingface.co/datasets/open-reaction-database/ord-data/resolve/93475c46949f9218e1dfb6624096025135db2add/data/fe/ord_dataset-feaf1b793c6d408aaec1cac7cc3ceadc.parquet"},"publication":{"slug":"ord-publication-91c8bf15879e5ce2","title":"Literature experiment — 10.1021/jo9010624","source_type":"paper","doi":"10.1021/jo9010624","url":"https://doi.org/10.1021/jo9010624","note":"Publication DOI reported by the Open Reaction Database. Experimental record data adapted under CC BY-SA 4.0; https://creativecommons.org/licenses/by-sa/4.0/"},"license":"CC-BY-SA-4.0","license_url":"https://creativecommons.org/licenses/by-sa/4.0/","attribution":"Open Reaction Database contributors and the cited original publications","changes":["Bounded selection across datasets and publications","Deduplicated exact transformations across conditions","Canonicalized molecular structures using RDKit; calculated identifiers, formulae and molecular weights","Explicitly incomplete directed branches for all recorded reactants and positively measured products","Removed submitter account and contact fields from provenance; retained scientific input and outcome fields"]}