Acetamide → 3-(2-Methyl-5-propyl-oxazol-4-yl)-benzoic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10](=O)[CH:11](Br)[CH2:12][CH2:13][CH3:14])[CH:5]=1.[C:18]([NH2:21])(=[O:20])[CH3:19]>>[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[N:21]=[C:18]([CH3:19])[O:20][C:11]=2[CH2:12][CH2:13][CH3:14])[CH:5]=1Participants
3
Procedure
A sample of rac-3-(2-bromo-pentanoyl)-benzoic acid methyl ester (1.50 g) and acetamide (0.89 g) were heated together to 130° C. for 15 h. The mixture was partitioned between AcOEt and brine, the organic layer was dried and evaporated and the residual oil was chromatographed on silica gel using AcOEt/hexane (1:3) as eluent to give 3-(2-methyl-5-propyl-oxazol-4-yl)-benzoic acid methyl ester (0.47 g) as a light-yellow oil.
Workup
- customThe mixture was partitioned between AcOEt and brine
- customthe organic layer was dried