4-Fluorobenzamide → Ethyl[2-(4-fluorophenyl)-5-methyl-1,3-oxazol-4-yl]acetate
Reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=1.Br[CH:12]([CH3:21])[C:13](=O)[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]>C1(C)C=CC=CC=1>[CH2:18]([O:17][C:15](=[O:16])[CH2:14][C:13]1[N:8]=[C:6]([C:5]2[CH:9]=[CH:10][C:2]([F:1])=[CH:3][CH:4]=2)[O:7][C:12]=1[CH3:21])[CH3:19]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 140 °C
Procedure
A suspension of 4fluorobenzamide (12.9 g) and ethyl 4bromo-3-oxopentanoate (Chem Abs No. 3618769-6; 5.24 g) in anhydrous toluene (120 ml) was heated at 140° C. for 19 h, using a Dean-Stark trap. The solution was allowed to cool, filtered, and the residual solid washed with toluene (30 ml). The combined filtrate and washings were concentrated in vacuo to give a brown oil, which was purified by Biotage flash chromatography on silica gel (90 g column), eluting with ethyl acetate:cyclohexane (5:95, 7.5:92.5, 10:90), to give the title compound as a yellow solid (2.98 g).