Dimethyl Sulfoxide → 5-(Tert-butyldimethylsilyloxy)cyclooctanone

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Reaction Conditions

Reaction Steps

A solution of 4.5 g (58 mmol) of dimethyl sulphoxide in 25 mL dichloromethane was added dropwise to a stirred solution of 3.7 g (29 mmol) of oxalyl chloride in 50 mL of dichloromethane at −78° C. The solution was stirred for 30 minutes at −78° C. and then 5.0 g (19.3 mmol) of cis-5-(tert-butyl-dimethyl-silanyloxy)-cyclooctanol (57) in 30 mL of dichloromethane was added dropwise keeping the temperature at −78° C. After stirring for 30 minutes, 9.8 g (97 mmol) of triethylamine was added dropwise and the temperature allowed to warm to −30° C. Further 50 mL of dichloromethane were added and the solution stirred for 1 h at −30° C. With stirring 300 mL of a saturated ammonium chloride solution were added portionwise and then the organic layer was separated. After washing with further ammonium chloride solution, the organic phase was dried over magnesium sulfate, filtered and evaporated to give 5.0 g of the desired product as a yellow oil which was used without purification. Rt=1.96 min (Method C). Detected mass: 257.3 (M+H+).

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