Dimethyl Sulfoxide → 4-Ethyl-2-(4-trifluoromethyl-phenyl)-oxazole-5-carbaldehyde
Reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([C:13]1[N:14]=[C:15]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=2)[O:16][C:17]=1[CH2:18][OH:19])[CH3:12].C(N(CC)CC)C>C(Cl)Cl>[CH2:11]([C:13]1[N:14]=[C:15]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=2)[O:16][C:17]=1[CH:18]=[O:19])[CH3:12]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a solution of oxalyl chloride (2.0M/DCM, 3.52 mL, 7.04 mmloe) in DCM (50 mL), is injected DMSO (0.998 mL, 14.1 mmole) and stirred for 15 minute at −78° C. A solution of [4-Ethyl-2-(4-trifluoromethyl-phenyl)-oxazol-5-yl]-methanol (1.59 g, 5.86 mmole) in DCM (10 mL) is then added. After stirred for 30 minutes, triethyl amine (4.08 mL, 29.3 mmole) is added. The reaction is kept at −78° C. for another 30 minutes, then warmed up to room temperature for 2 hours, washed with brine (3×50 mL), dried over Na2SO4, filtered and concentrated. The crude product is purified by flash chromatography (silica gel, 10% ethyl acetate in hexane) and concentrated to provide the titled compound as a white solid. Mass [EI+] 270 (M+H)+.
Workup
- stirringAfter stirred for 30 minutes
- waitThe reaction is kept at −78° C. for another 30 minutes
- temperaturewarmed up to room temperature for 2 hours
- washwashed with brine (3×50 mL)
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customThe crude product is purified by flash chromatography (silica gel, 10% ethyl acetate in hexane)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-77c4c0035ae74717bfa6aff3702bb290
- Source dataset
- uspto-grants-2006_12
- Patent number
- US07153878B2
Reaction notes
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