Boron trifluoride etherate → Diethyl-4-(mercaptomethyl)-1,3-dithiolane-2,2-dipropanoate

反応式

[SH:1][CH2:2][CH:3]([SH:6])[CH2:4][SH:5].O=[C:8]([CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12].B(F)(F)F.CCOCC>C(Cl)Cl>[CH2:14]([O:13][C:11](=[O:12])[CH2:10][CH2:9][C:8]1([CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[S:6][CH:3]([CH2:4][SH:5])[CH2:2][S:1]1)[CH3:15]

参加物

実験手順

A stirred solution of 1,2,3-trimercaptopropane (10.0 g, 0.071 mol) and diethyl 4-oxopimelate (16.43 g, 0.071 mol) in methylene chloride (300 ml) under nitrogen atmosphere was treated with boron trifluoride etherate (2 ml). After stirring for 3 days at room temperature, the reaction was quenched by addition of 200 ml of 5% sodium bicarbonate solution. The organic phase was separated and dried over anhydrous sodium sulfate. The drying agent was filtered and the filtrate concentrated on the rotary evaporator. The residue was chromatographed on silica gel using 5% ethyl acetate/hexane as eluent to give 10 g (40%) of the title compound as an oil.