[CH2:1]([O:3][C:4](=[O:21])[C:5]([C:7]1[S:8][CH:9]=[CH:10][C:11]=1[NH:12][C:13]1[C:18]([CH3:19])=[CH:17][CH:16]=[CH:15][C:14]=1[Cl:20])=O)[CH3:2].B([O-])=O.[Na+]>CN(C)C=O>[CH2:1]([O:3][C:4](=[O:21])[CH2:5][C:7]1[S:8][CH:9]=[CH:10][C:11]=1[NH:12][C:13]1[C:18]([CH3:19])=[CH:17][CH:16]=[CH:15][C:14]=1[Cl:20])[CH3:2]0.32 g (1 mmole) of 3-(2-chloro-6-methylanilino)-2-thiophenglyoxylic acid ethyl ester and 1 g of sodium boranate are warmed to 80° in 10 ml of dimethylformamide for 2 hours. The mixture is then poured onto water and washed with diethyl ether, and the aqueous phase is acidified and extracted with ethyl acetate. Concentration of the organic phase and column chromatography (silica gel/methylene chloride) give, in the first fraction, 3-(2-chloro-6-methylanilino)-2-thiophenacetic acid ethyl ester.
Wird geladen…