2-Butyn-1-ol → HCID 70083899, compound

Participants

Reaction Steps

The ethyl(3-chlorophenyl)[(4-hydroxyphenyl)sulfanyl]acetate (4.2 g, 13 mmol) was stirred with THF (100 ml) in a dried two-necked flask under inert conditions. The 2-butyn-1-ol (0.97 ml, 13 mmol) and 1,1′(azodicarbonyl)dipiperidine (3.94 g, 15.6 mmol). Tributylphosphine (3.90 ml, 15.6 mmol) was added dropwise at 0° C. The reaction mixture was allowed to stir at room temperature under nitrogen for 2 hours before it was concentrated. The residue was triturated with ether and the filtrate was concentrated, Ethyl{[4-(2-butynyloxy)phenyl]sulfanyl}(3-chlorophenyl)acetate was isolated as a yellow oil (4.08 g) after silica-gel column chromatography, using methylene chloride as the mobile phase. Yield 84%; MS(EI): 375 (M+H)+

Provenance & Evidence