[CH3:1][C:2]1[CH:15]=[CH:14][C:5]2[S:6][CH:7]=[C:8]([CH2:9][C:10]([O:12][CH3:13])=[O:11])[C:4]=2[CH:3]=1.[H-].[Na+].Cl.CN(C)[CH:21]=[O:22]>C(OC)=O>[CH3:1][C:2]1[CH:15]=[CH:14][C:5]2[S:6][CH:7]=[C:8]([C:9](=[CH:21][OH:22])[C:10]([O:12][CH3:13])=[O:11])[C:4]=2[CH:3]=1
A solution of 79.7 g of methyl 5-methyl-3-benzo[b]thienylacetate in 200 ml of dimethylformamide and 200 ml of methyl formate is slowly added dropwise to a suspension of 10.4 g of sodium hydride in 100 ml of dimethylformamide. The reaction mixture is stirred for 2 hours at room temperature and then acidified with dilute hydrochloric acid, and this is then extracted with ethyl acetate. The organic phase is washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. In this manner, methyl α-(5-methyl-3-benzo[b]thienyl)-β-hydroxyacrylate is obtained as the crude product which is used unpurified as the starting material in the next process step.
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