Water → HCID 18546536, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 3-methylthio-1-propanol (17) (12.5 g, 117.7 mmol) and triethylamine (17.8 g, 177.0 mmol) in dry CH2Cl2 (110 mL) cooled in an ice bath (0-5° C.), a solution of acryloyl chloride (21.3 g, 235.0 mmol) in dry CH2Cl2 (30 mL) was added drop-wise with stirring over a period of 2.5 hours. The reaction mixture was warmed to a room temperature, and then diluted with more CH2Cl2 (225 mL), and poured into water (250 mL). The CH2Cl2 layer was washed with saturated aqueous NaHCO3 solution (2×175 mL), and water (2.225 mL). Evaporation of the dried (Na2SO4) organic layer gave a yellow oil. Purification by column chromatography, (silica gel, hexanes, 10 wt % ether/hexanes) produced a clear oil compound 18 (11.4 g, 60 wt %), namely 3-methylthio-1-propyl acrylate (18).

Provenance & Evidence