Methanol → Tetrahydropyranyl ether

To a solution of 100.0 g (0.2557 mole) of methyl hyodeoxycholate and 5.68 g of p-toluenesulfonic acid in 2000 ml of p-dioxane was added 153.7 g (1.62 mole, 148.6 ml) of dihydropyran over a period of 30 min under argon atmosphere. After stirring overnight at room temperature, the pH of the solution was adjusted to approximately pH 8 by the addition of 55 ml of 50/50 methanol/29% ammonium hydroxide. The solution was concentrated to a yellow oil under reduced pressure and the residue stirred in heptane 4 hr, then filtered to remove the precipitated p-toluenesulfonic acid. The filtrate was heated with charcoal, filtered, and evaporated to yield 116.8 g (80%) of the di-tetrahydropyranyl ether as a colorless viscous oil.

1. concentrationThe solution was concentrated to a yellow oil under reduced pressure
2. stirringthe residue stirred in heptane 4 hr
3. filtrationfiltered
4. customto remove the precipitated p-toluenesulfonic acid
5. temperatureThe filtrate was heated with charcoal
6. filtrationfiltered
7. customevaporated

ORDレコード

ord-88fbc7477517481f87ee1a5dc2de7734

出典データセット

uspto-grants-1980_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US04217279