[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([CH2:10][CH2:11]OS(C)(=O)=O)[C:4]=2[CH2:3][CH2:2]1.[C-:17]#[N:18].[Na+]>CS(C)=O.O>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([CH2:10][CH2:11][C:17]#[N:18])[C:4]=2[CH2:3][CH2:2]1A solution of methanesulfonic acid 2-(2,3-dihydrobenzofuran-4-yl)-ethyl ester (1.71 g) in dimethylsulfoxide (14 ml) was treated with sodium cyanide (381 mg) and heated at 80° for 1 h. The suspension was cooled to 20°, diluted with water (14 ml) and extracted with ethyl acetate (2×17 ml). The combined extracts were washed with 5% aqueous sodium chloride (17 ml), dried (Na2SO4) and the solvent evaporated to give the title compound (1.22 g) as a brown oil which crystallised on standing.
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