Diethyl Ether → 2-Trimethylsilyloxy-2-pentene

In 500 mL of dichloromethane, was dissolved 22.0 mL (207 mmol) of 2-pentanone. While stirring the resulting solution in an ice bath, 44 mL (317 mmol) of triethylamine was added to the solution, and then, 42 mL (232 mmol) of trimethylsilyl trifluoromethanesulfonate was added dropwise to the solution. After the addition of trimethylsilyl trifluoromethanesulfonate, the mixture was stirred for 1 hour at room temperature, poured into ether (500 mL)/a saturated aqueous sodium hydrogencarbonate solution (300 mL) so as to extract the ether layer. The ether layer was washed with saturated sodium chloride water and water, dried over sodium sulfate anhydride, filtered, and concentrated. The residue was distilled under normal pressure to collect fractions of 110 to 125° C. As a result, 8.43 g (53.2 mmol, 49.4%) of 2-trimethylsilyloxy-2-pentene was obtained. According to a similar method, 5.33 g (33.6 mmol, 32.3%) of 2-trimethylsilyloxy-2-pentene was obtained from 11.0 mL (103.8 mmol) of 2-pentanone.

1. stirringthe mixture was stirred for 1 hour at room temperature
2. extractionto extract the ether layer
3. washThe ether layer was washed with saturated sodium chloride water and water
4. dry with materialdried over sodium sulfate anhydride
5. filtrationfiltered
6. concentrationconcentrated
7. distillationThe residue was distilled under normal pressure
8. customto collect fractions of 110 to 125° C

ORD-Eintrag

ord-c16bb04a563b429eb2cd9a94e017979e

Quelldatensatz

uspto-grants-2001_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06215016B1