Hydrochloric Acid → Methyl 3-(oxan-4-yl)-3-oxopropanoate

Temperatur

7.5 °C

In a flask made of glass having an inner volume of 500 ml and equipped with a stirring device, a thermometer, a dropping funnel and a distillation device were charged 35.0 g (273 mmol) of 4-acetyltetrahydropyran synthesized in the same manner as in Reference example 2, 280.0 g (3.1 mol) of dimethyl carbonate and 16.3 g (302 mmol) of sodium methoxide, and the mixture was reacted at 80 to 85° C. for 2 hours with distilling by-producing methanol off. After completion of the reaction, the reaction mixture was cooled to 5 to 10° C., and to the reaction mixture were added 175 ml of toluene, 55 ml (330 mmol) of 6 mol/l hydrochloric acid and 35 ml of water in this order. After the organic layer was separated, the aqueous layer was extracted twice with 70 ml of toluene. The organic layer was concentrated under reduced pressure, and the concentrate was purified by silica gel column chromatography (Fluent; hexane/ethyl acetate=1/1 (volume ratio)) to give 40.9 g (Isolation yield: 76%) of methyl 3-(4-tetrahydropyranyl)-3-oxopropanoate with a purity of 93.9% (analytical value by differential diffractometry) as a colorless liquid.

1. customIn a flask made of glass
2. customequipped with a stirring device
3. customthe mixture was reacted at 80 to 85° C. for 2 hours
4. distillationwith distilling
5. customby-producing methanol off
6. customAfter completion of the reaction
7. customAfter the organic layer was separated
8. extractionthe aqueous layer was extracted twice with 70 ml of toluene
9. concentrationThe organic layer was concentrated under reduced pressure
10. customthe concentrate was purified by silica gel column chromatography (Fluent; hexane/ethyl acetate=1/1 (volume ratio))

ORD-Eintrag

ord-037b2190d1ed4b2c8f4fd39f39619278

Quelldatensatz

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07741497B2