Dimethyl Sulfoxide → HCID 131728082, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of oxalyl chloride (0.977 mL, 11.2 mmol) in dry CH2Cl2 (20 mL) at −78° C. was added dropwise DMSO (1.19 mL, 16.8 mmol) in dry CH2Cl2 (2.0 mL) over a period of 10 minutes and the mixture was stirred at −78° C. for 15 minutes. A solution of [3-(tert-butyl-diphenyl-silanyloxymethyl)-1,2,2-trimethyl-cyclopentyl]-methanol (2) (2.30 g, 5.6 mmol) in dry CH2Cl2 (6.0 mL) was added dropwise at −78° C. over a period of 30 minutes and the reaction mixture was stirred at −78° C. for 30 minutes. Triethylamine (3.9 mL, 28.0 mmol) was added dropwise at −78° C. over a period of 10 minutes and the reaction mixture was stirred at −78° C. for 1 hour. The temperature of the mixture is allowed to rise to −10° C. over a period of 3.5 hours and cold H2O (60 mL) was added. The organic layer was separated, the aqueous layer was extracted with Et2O (3×60 mL) and the combined organic layers were dried over anhydrous MgSO4. The solvents were removed in vacuo and the residue was purified over silica (n-hexane/ ethyl acetate, 98:2) to afford 2.21 g (97% yield) of the desired product (4) as a viscous oil which was characterized as follows:

Provenance & Evidence