Dimethyl Sulfoxide → 1-Phenyl-2-(pyridin-2-yl)propan-1-one
Reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[C:11]1([CH:17]([OH:26])[CH:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)[CH3:19])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C>ClCCl>[C:11]1([C:17](=[O:26])[CH:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)[CH3:19])[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1Participants
Conditions
- Temperature
- 0 °C
Procedure
A solution of DMSO (5.5 mL, 77.5 mmol) in dichloromethane (10 mL) is added drop wise to a solution of oxalyl chloride (3.3 mL, 39.0 mmol) in dichloromethane (100 mL) with the internal temperature under −60° C. The reaction mixture is stirred for 15 minutes and then a solution of 1-phenyl-2-(pyridin-2-yl) propan-1-ol (2) (7.0 g, 32.8 mmol) in dichloromethane (10 mL) is added slowly to keep the internal temperature under −60° C. After 30 minutes, triethylamine (22.3 mL, 0.16 mol) is added slowly at −78° C. After 15 minutes, the reaction is allowed to warm up to 0° C. for 30 minutes and then quenched with water. The mixture is separated and the aqueous phase is extracted with dichloromethane (2×50 mL). The extracts are combined, washed with brine, dried, concentrated and purified by column chromatography (hexane/ethyl acetate 10:1 to 4:1) to give 3 (6.4 g, 91%) as a yellow oil. 1H NMR (300 MHz, CDCl3): δ 1.51-1.54 (m, 3H), 4.84-4.92 (m, 1H), 7.03-708 (m, 1H), 7.18-7.20 (m, 2H), 7.30-7.35 (m, 1H), 7.40-7.43 (m, 1H), 7.52-7.57 (m, 1H), 7.95-7.98 (m, 2H), 8.47-8.48 (m, 1H).
Workup
- customunder −60° C
- waitAfter 30 minutes
- waitAfter 15 minutes
- customquenched with water
- customThe mixture is separated
- extractionthe aqueous phase is extracted with dichloromethane (2×50 mL)
- washwashed with brine
- customdried
- concentrationconcentrated
- custompurified by column chromatography (hexane/ethyl acetate 10:1 to 4:1)
Sources & evidence
- ORD record
- ord-7db636fa3752479888a9094d37dfa9f1
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08013165B2
Reaction notes
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