4-Toluenesulfonyl chloride → (+/-)-2,3,6,7,8,9-Hexahydronaphtho[1,2-b]furan-2-ylmethyl 4-methylbenzenesulfonate

Participants

Reaction Conditions

Reaction Steps

To a solution of (±)-2,3,6,7,8,9-hexahydronaphtho[1,2-b]furan-2-ylmethanol (1.37 g, 6.71 mmol) in dichloromethane (50 mL) was added p-toluenesulfonyl chloride (2.56 g, 13.41 mmol), 4-(dimethylamino)pyridine (0.164 g, 1.34 mmol), and triethylamine (1.70 g, 16.77 mmol) and the reaction mixture was allowed to stir at 40° C. for 12 h. The reaction mixture was diluted with water (250 mL) and the aqueous layer extracted with dichloromethane (2×150 mL). The combined organic extracts were washed with saturated aqueous sodium chloride, dried (magnesium sulfate), and the solvent was removed in vacuo to provide a crude oil. Purification by flash column chromatography (silica, ethyl acetate:hexanes 1:5) gave 2.05 g (85%) of (±)-2,3,6,7,8,9-hexahydronaphtho[1,2-b]furan-2-ylmethyl 4-methylbenzenesulfonate as a colorless oil. Rf=0.5 (silica, ethyl acetate:hexanes 1:4); Anal. calcd. for C20H22O4S: C, 67.01; H, 6.19. Found: C, 66.50; H, 6.27.

Provenance & Evidence