Pyridine → HCID 86612733, compound

Participants

Reaction Steps

To an ice cold solution of 4.6 g (16.4 mmol) (2R,9S)-9-benzyloxydecane-1,2-diol in 50 ml abs. pyridine was slowly added a solution of 2.9 g (15 mmol) p-toluene sulfonyl chloride in 20 ml abs. pyridine. Stirring was continued for 5 h at 0° C. and 12 h at 4° C. Subsequently, 150 ml ice water (brought to pH 5 with 0.1% hydrochloric acid) were added and 60 ml diethyl ether. Subsequently, the aqueous layer was extracted four times with 120 ml diethyl ether. The combined organic layers were washed three times with 100 ml of an aqueous, saturated solution of copper-II-sulphate and two times with 100 ml brine. The organic layer was dried over magnesium sulphate and concentrated in vacuo. Flash chromatography (10% ethyl acetate in hexane) furnished 4.6 g (10.5 mmol, 64%) (2R,9S)-9-benzyloxy-1 (p-tolylsulfonyloxy)decane-2-ol.

Provenance & Evidence