Tin tetrachloride → HCID 178527225, compound

Participants

Reaction Conditions

Reaction Steps

To 600 mg (2.56 mmol) of 8-tert-butyl-4,4-dimethyl-thiochromane and 0.38 g (2.84 mmol) of (+/-) tetrahydro-3-furoic acid chloride [which is prepared by reacting 1.5 g (12.9 mmol) (+/-) tetrahydro-3-furoic acid with 1.38 mL (15.5 mmol) oxalyl chloride in 40 mL benzene at 50° C. for 1 hour followed by concentration of the volatiles under reduced pressure] in 10 mL benzene at 0° C. is added 0.32 mL (2.73 mmol) tin tetrachloride. The reaction is allowed to stir 1 hour at 0° C. and is then diluted with ether and washed with water and sodium chloride. The product is purified by flash silica gel chromatography, eluting with 7:3 hexane:ethyl acetate to give 257 mg of 8-tert-butyl-4,4-dimethyl-6-(1-oxo-1-(3-tetrahydrofuryl)methylthiochromane.

Provenance & Evidence