Tetrahydro-4H-pyran-4-one → 4-(Methoxymethylidene)oxane

Tetrahydro-4H-pyran-4-one (5.00 g, 50 mmol) was dissolved in tetrahydrofuran (250 ml) and cooled in an ice-water bath. To this solution was added n-butyl lithium (24 ml of a 2.5M solution in hexane, 60 mmol) and the reaction mixture was then allowed to warm to room temperature and stirred for 1 hour. This was then cooled to 0° C. and a solution of (methoxymethyl)triphenyl phosphonium chloride (25.6 g, 75 mmol) in tetrahydrofuran (10 ml) was added and the reaction stirred for 30 minutes. The reaction mixture was then concentrated under reduced pressure and the residue triturated with diethyl ether (10×), decanting the supernatant each time. The combined supernatants were then evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using an elution gradient of pentane:ethyl acetate (95:5 to 90:10) to provide the title compound, 1.80 g.

1. temperaturecooled in an ice-water bath
2. temperatureThis was then cooled to 0° C.
3. stirringthe reaction stirred for 30 minutes
4. concentrationThe reaction mixture was then concentrated under reduced pressure
5. customthe residue triturated with diethyl ether (10×)
6. customdecanting the supernatant each time
7. customThe combined supernatants were then evaporated under reduced pressure
8. customThe residue was purified by column chromatography on silica gel using an elution gradient of pentane:ethyl acetate (95:5 to 90:10)

ORD record

ord-1c597183fd6b44beba3640f8f3493726

Source dataset

uspto-grants-2007_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07217714B1