p-Toluenesulfonic acid → (R)-2-(tetrahydro-pyran-2-yloxy)-propionic acid methyl ester

Methyl (R)-(+)-lactate (25.0 g) was dissolved in dichloromethane (250 ml), to which was added, under ice-cooling, p-toluenesulfonic acid.hydrate (456 mg). To the mixture was then added dropwise 3,4-dihydro-2H-pyran (24.2 g) during 30 minutes, which was stirred for one hour under ice-cooling. To the reaction mixture was added a 5% aqueous solution of sodium hydrogen carbonate (50 ml), and the mixture was stirred vigorously, followed by separating the organic layer. The organic layer was further washed with a 5% aqueous solution of sodium hydrogen carbonate, which was dried over anhydrous magnesium sulfate, followed by distilling off the solvent under reduced pressure to leave methyl (2R)-2-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)propionate (42.7 g) as a pale yellow oily product.

1. additionwas added, under ice-
2. temperaturecooling
3. temperaturecooling
4. stirringthe mixture was stirred vigorously
5. customby separating the organic layer
6. washThe organic layer was further washed with a 5% aqueous solution of sodium hydrogen carbonate, which
7. dry with materialwas dried over anhydrous magnesium sulfate
8. distillationby distilling off the solvent under reduced pressure

ORD 기록

ord-7a16b6ea7d494e3898485df5ff9ac16c

출처 데이터셋

uspto-grants-1995_04

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US05405861