Water → HCID 63115554, compound

Temperature

80 °C

To a suspension of sodium hydride (commercially available, for example, from Aldrich) (60% dispersion in mineral oil; 800 mg, 20 mmol) in dry DMF (30 ml) was carefully added cyclopentyl mercaptan (commercially available, for example, from Aldrich and/or Alfa Aesar) (2.14 ml, 20 mmol). The resultant suspension was stirred at room temperature, under nitrogen for 15 min before adding 3-bromopropanol (commercially available, for example, from Aldrich) (1.81 ml, 20 mmol). The mixture was then stirred under nitrogen and heated to 80° C. overnight. Water (20 ml) was cautiously added to the reaction mixture, followed by diethyl ether (50 ml). The aqueous solution was extracted with diethyl ether (2×50 ml). The combined organic solutions were washed with water (100 ml) and brine (100 ml) and concentrated in vacuo to leave a yellow oil, which was purified by flash chromatography on silica eluting with cyclohexane-EtOAc (3:1) increasing to (1:1). The solvents were removed in vacuo to afford the title compound (2.18 g). LCMS RT=2.61 min, ES+ve m/z 161 (M+H)+.

1. extractionThe aqueous solution was extracted with diethyl ether (2×50 ml)
2. washThe combined organic solutions were washed with water (100 ml) and brine (100 ml)
3. concentrationconcentrated in vacuo
4. customto leave a yellow oil, which
5. customwas purified by flash chromatography on silica eluting with cyclohexane-EtOAc (3:1)
6. temperatureincreasing to (1:1)
7. customThe solvents were removed in vacuo

ORD record

ord-bc8f405788d04f059a49902b0d43ace1

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07884114B2