Water → Pentan-3-yl methanesulfonate

Temperature

0 °C

To a colorless solution of 88.15 g 3-pentanol (1.0 mol) in 150 ml pyridine were added under stirring at 0° C. 126.0 g methanesulfonyl chloride (1.1 mol) over 1 h. After warming up (15 min.) and stirring at room temperature for 1 h, 50 ml deionized water were added all at once and stirring at room temperature was continued for 1 h. The reaction mixture was diluted with 500 ml ethyl acetate and washed with 800 ml 1N HCl and 250 ml 10% brine. Both aqueous layers were extracted sequentially with 250 ml ethyl acetate. After drying the combined organic layers over ca. 20 g Na2SO4, the solvent was removed on the rotary evaporator (50° C./≧1 mbar) affording 154.4 g (92.9%) yellow, oily title product, which could be used in the next step without purification.

1. temperatureAfter warming up (15 min.)
2. stirringstirring at room temperature for 1 h
3. additionwere added all at once and
4. stirringstirring at room temperature
5. washwashed with 800 ml 1N HCl and 250 ml 10% brine
6. extractionBoth aqueous layers were extracted sequentially with 250 ml ethyl acetate
7. dry with materialAfter drying the combined organic layers over ca. 20 g Na2SO4
8. customthe solvent was removed on the rotary evaporator (50° C./≧1 mbar)
9. customaffording 154.4 g (92.9%) yellow
10. customoily title product, which could be used in the next step without purification

ORD record

ord-18d7d0bd946a4da4b96c9cc6ccb9e674

Source dataset

uspto-grants-2003_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06518048B2