Water → HCID 18546536, compound

Temperature

2.5 °C

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).

1. temperatureThe reaction mixture was warmed to a room temperature
2. washThe CH2Cl2 layer was washed with saturated aqueous NaHCO3 solution (2×175 mL), and water (2.225 mL)
3. customEvaporation of the
4. dry with materialdried (Na2SO4) organic layer
5. customgave a yellow oil
6. customPurification by column chromatography, (silica gel, hexanes, 10 wt % ether/hexanes)

ORD record

ord-342eb16a2bb8467e97e54fc13576a8f8

Source dataset

uspto-grants-2000_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06107365