Phenol, 2-(2-propenyloxy)- → (2R)-3-(o-Allyloxyphenoxy)-1,2-epoxypropane

Temperature

0 °C

o-Allyloxyphenol (1.0 g) was dissolved in THF (10 ml) under nitrogen atmosphere and the solution was cooled to 0° C. Potassium fluoride (1.55 g) and tetrabutyl ammonium fluoride (0.2 g) were added thereto and the mixture was stirred for 1 hour. Then (S)-glycidyl M-nitrobenzenesulfonate (1.73 g, 99.3% e.e.) was added thereto and the mixture was stirred for 40 hours at the same temperature. After the reaction water was added to the mixture, the mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, condensed and the residue was subjected to silica gel chromatography (hexane/ethyl acetate; 3:2) to give 0.96 g of (R)-3-(o-allyloxyphenoxy)-1,2-epoxypropane (yield 70%, optical purity 95.9% e.e.) as a colorless oil.

1. stirringthe mixture was stirred for 40 hours at the same temperature
2. additionwas added to the mixture
3. extractionthe mixture was extracted with ethyl acetate
4. dry with materialdried over anhydrous magnesium sulfate, condensed

ORD record

ord-11b7878206174909a359773aa0385284

Source dataset

uspto-grants-2000_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06057476