[H-].[Na+].[CH3:3][C:4]1[CH:8]=[CH:7][S:6][C:5]=1[CH:9]=[CH:10][C:11]([OH:13])=[O:12].[H][H].[CH2:16](Br)[C:17]#[CH:18]>CN(C=O)C>[CH3:3][C:4]1[CH:8]=[CH:7][S:6][C:5]=1[CH:9]=[CH:10][C:11]([O:13][CH2:18][C:17]#[CH:16])=[O:12]
At 10° C., 0.9 g of sodium hydride was added to a solution of 6.2 g of 3-(3-methylthiophen-2-yl)-propenoic acid in 100 ml of absolute DMF. When no more hydrogen evolved, 4.9 g of propargyl bromide was dripped in at room temperature and the mixture was then heated at 50° C. for 3 hours. The reaction mixture was poured onto icewater, the aqueous phase was extracted three times with ethyl acetate, and the combined organic extracts were dried over Na2SO4. After removal of the solvent under reduced pressure, the residue was recrystallized from ethanol. There was obtained 3.9 g of propargyl 3-(3-methylthiophen-2-yl)-propenoate of melting point 84' to 86° C.
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