Hydrochloric Acid → Methyl 3-(4-tetrahydropyranyl)-2-methyl-3-oxopropanoate

Temperature

7.5 °C

In a flask made of glass having an inner volume of 100 ml and equipped with a stirring device, a thermometer, a dropping funnel and a distillation device were charged 1.28 g (9 mmol) of 4-propionyltetrahydropyran synthesized in the same manner as in Example 5, 16.0 g (180 mmol) of dimethyl carbonate and 1.2 g (22 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., to the reaction mixture were added 50 ml of ethyl acetate, 3.4 g (24 mmol) of 6 mol/l hydrochloric acid and 15 ml of water in this order. After the organic layer was separated, the aqueous layer was extracted twice with 50 ml of ethyl acetate. The organic layer was concentrated under reduced pressure, and the concentrate was purified by silica gel column chromatography (Eluent; hexane/ethyl acetate=3/1 (volume ratio)) to give 0.60 g (Isolation yield: 33%) of methyl 3-(4-tetrahydropyranyl)-2-methyl-3-oxopropanoate 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 50 ml of ethyl acetate
9. concentrationThe organic layer was concentrated under reduced pressure
10. customthe concentrate was purified by silica gel column chromatography (Eluent; hexane/ethyl acetate=3/1 (volume ratio))

ORD record

ord-6bb4a67a7e164193a05eb7eefa344937

Source dataset

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07741497B2