Dimethyl Sulfoxide → HCID 87281415, compound

Participants

Reaction Steps

A turbid solution of 1.245 g (3.58 mmol) phosphonitrilic chloride trimer in 20 ml dichloromethane was cooled to −75° C. To this mixture 1.02 ml (14.32 mmol) DMSO were added, and stirring was continued for 1 h. Then a suspension of 1.28 g (3.58 mmol; 1 eq.; example 37.1) [rac]-2-[2-(4-chloro-phenyl)-4,5,6,7-tetrahydro-2H-indazol-3-yl]-2-cyclohexyl-ethanol in 50 ml dichloromethane was added dropwise over 10 min to the turbid reaction mixture, keeping the temperature below −60° C. The reaction mixture was then stirred 1 h at −75° C. Then the mixture was stirred in an ice-bath, and at 0° C. 2.50 ml (17.91 mmol) triethylamine were added. The solution was stirred 1.5 h at 0° C. and then at ambient temperature overnight. The reaction mixture was poured onto 120 ml water, extracted 3 times with dichloromethane. The organic layers were washed with water and brine, dried over MgSO4, filtered and evaporated to give the crude product which was purified on a 20 g silica gel column using a gradient from heptane (A) and ethyl acetate (B) to give the title aldehyde.

Provenance & Evidence