Dimethyl Sulfoxide → HCID 15661440, compound

Participants

Reaction Steps

Dichloromethane (5 ml) was cooled to -60° C. under N2, oxalyl chloride (1.65 ml, 1M soln in CH2Cl2, 1.1 eq) was added followed by DMSO (234 μl in 1 ml of (CH2Cl2). The resulting solution was stirred at -60° for 10 minutes. The 3-bromo-1-acetoxymethyl-9-fluorenol (0.480 g) in a suspension of CH2Cl2 (2 ml) was added dropwise and the solution stirred at -60° for 0.5 hour. Triethylamine (1.06 ml) was added dropwise and the solution stirred at -60° for 15 minutes. The cooling bath was removed and water (5 ml) was added and the reaction mixture stirred at room temperature for 20 minutes. The organic phase was separated and the aqueous phase was extracted with EtOAc, the combined organic extract was dried and evaporated which gave product, one spot on tlc, used without further purification in the next step. ##STR39##

Provenance & Evidence