Triethylamine → HCID 19896626, compound

Participants

Reaction Steps

A cold (5° C.) solution of 4-methylthiobenzyl alcohol (3.0 g, 19.45 mmol) in CH2Cl2 (60 mL) was treated with triethylamine (2.17 g, 21.4 mmol) and methanesulfonyl chloride (2.45 g, 21.4 mmol). The mixture was stirred for 1 h, then diluted with Et2O and filtered. The filtrate was evaporated to dryness, redissolved in CH3CN and treated with NaN3 (1.52 g, 23.34 mmol) and (Bu)4NCl (0.150 g). The mixture was stirred at room temperature for 18 h, then diluted with ethyl acetate and washed successively with water, dilute NaHCO3 and brine, dried (MgSO4), and finally evaporated. The crude compound was purified by silica gel chromatography (eluted with petroleum ether and CH2Cl2) to afford 2.79 g (80.0%) of the title product as a mobile oil.

Provenance & Evidence