Water → 2-(4-chlorophenyl)-2-[(1R)-1-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)ethyl]oxirane

Trimethylsulfoxonium iodide (67.8 g) was added portionwise to an ice-cooled dispersion of 60% sodium hydride in oil (11.8 g) in dimethyl sulfoxide (450 ml) under nitrogen atmosphere. After stirring for 45 minutes at room temperature, the mixture was again cooled in an ice-water bath. To the mixture was added dropwise a solution of (2R)-4'-chloro-2-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)propiophenone (69 g) in dimethylsulfoxide (100 ml) over the period of 45 minutes, followed by stirring for 2 hours at room temperature. Cold water (600 ml) was added to the reaction mixture, which was then extracted three times with ethyl acetate (400 ml, 300 ml and 300 ml). The combined extracts were washed twice with water (100 ml) and once a saturated aqueous saline solution (100 ml), dried over anhydrous magnesium sulfate and distilled under reduced pressure, thereby affording a crude product of 2-(4-chlorophenyl)-2-[(1R)-1-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)ethyl]oxirane (74.5 g) as a pale yellow oily substance.

1. temperaturethe mixture was again cooled in an ice-water bath
2. stirringby stirring for 2 hours at room temperature
3. extractionwas then extracted three times with ethyl acetate (400 ml, 300 ml and 300 ml)
4. washThe combined extracts were washed twice with water (100 ml)
5. dry with materialonce a saturated aqueous saline solution (100 ml), dried over anhydrous magnesium sulfate
6. distillationdistilled under reduced pressure

ORDレコード

ord-e1cea4246ec0481ea3bdae85e3dcd0ce

出典データセット

uspto-grants-1996_02

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05495024