(R)-Methyl 2-(3-chlorophenyl)-2-hydroxyacetate → Methyl 3-chloro-alpha-oxobenzeneacetate
Reaction equation
C1C=CC(N=NC2C=CC(N)=NC=2N)=CC=1.Cl.[Cr](Cl)([O-])(=O)=O.[Cl:23][C:24]1[CH:25]=[C:26]([C@@H:30]([OH:35])[C:31]([O:33][CH3:34])=[O:32])[CH:27]=[CH:28][CH:29]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[Cl:23][C:24]1[CH:25]=[C:26]([C:30](=[O:35])[C:31]([O:33][CH3:34])=[O:32])[CH:27]=[CH:28][CH:29]=1Participants
Conditions
- Temperature
- 30 °C
Procedure
Pyridium chlorochromate (32.4 g, 150.00 mmol, 2.01 equiv.) was added to a solution of (R)-Methyl 2-(3-chlorophenyl)-2-hydroxyacetate (15 g, 74.77 mmol, 1.00 equiv) in dichloromethane (500 mL). The resulting solution was stirred at about 30° C. for about 2 hours, and then fresh pyridinium chlorochromate (16.4 g, 75.93 mmol, 1.02 equiv.) was added. The resulting solution was stirred at about 30° C. for about 16 hours, and then fresh pyridinium chlorochromate (16.4 g, 75.93 mmol, 1.02 equiv) was added. The resulting solution was stirred at about 30° C. for about 16 hours, and then concentrated in vacuo. The resulting crude residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether (1:20)) to give the title product as a yellow solid (13.8 g; yield=91%). 1H NMR (300 MHz, DMSO-d6) δ: 8.02 (t, J=1.8 Hz, 1H), 7.98 (m, 1H) 7.95 (m, 1H), 7.64 (d, J=7.8 Hz, 1H), 3.94 (s, 3H).
Workup
- stirringThe resulting solution was stirred at about 30° C. for about 16 hours
- stirringThe resulting solution was stirred at about 30° C. for about 16 hours
- concentrationconcentrated in vacuo
- customThe resulting crude residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether (1:20))
Sources & evidence
- ORD record
- ord-c167adf21bba4ba0b48fecf14afa069d
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09394239B2
Reaction notes
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