Mesityl oxide → Methyl α-(1,1-dimethyl-3-oxobutyl)-4-fluoro-3-methyl-β-oxobenzenepropanoate
Reaction equation
[F:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[O:7])=[CH:4][C:3]=1[CH3:15].[O:16]=[C:17]([CH:19]=[C:20]([CH3:22])[CH3:21])[CH3:18].C([O-])(O)=O.[Na+]>>[CH3:21][C:20]([CH3:22])([CH2:19][C:17](=[O:16])[CH3:18])[CH:8]([C:6](=[O:7])[C:5]1[CH:13]=[CH:14][C:2]([F:1])=[C:3]([CH3:15])[CH:4]=1)[C:9]([O:11][CH3:12])=[O:10]Participants
4
Procedure
A mixture of methyl 4-fluoro-3-methylbenzoylacetate (1a) (26.95g, 0.128 mol) and mesityl oxide (2) (19.3g, 0.192 mol) was kept at 0°-5° C. for 5 days, poured onto cold saturated NaHCO3 and extracted with ether. The combined extracts were washed with H2O and brine and dried (MgSO4). Removal of the volatiles in vacuo furnished 3a which was used without further purification.