Tributylphosphine → HCID 131729883, compound

Participants

Reaction Steps

A solution of 4.18 g of alcohol 184 (13.3 mmol) in 50 ml of anhydrous THF and 17 ml of anhydrous pyridine was added with 3.31 g of ortho-nitrophenyl selenocyanate (14.6 mmol, 1.1 eq.). Slow dropwise addition of 4.30 ml of tri-n-butylphosphine (17.3 mmol, 1.3 eq.) with cooling in an ice bath resulted in a dark-red solution. After stirring for 30 min at RT, the batch was diluted with 200 ml of MTBE and filtered over a small amount of silica gel. Concentrating the filtrate afforded a brownish-yellow residue that was purified using silica gel column chromatography (EE/CH 1:4), thereby isolating 6.06 g of the selenyl ether 47 (12.1 mmol, 92%) as an intensely yellow colored oil.

Provenance & Evidence