Methoxymethyl-triphenylphosphonium chloride → HCID 178445634, compound

Temperature

-50 °C

A mixture of 66.4 g (193.7 mmol) of methoxymethyltriphenyl phosphonium chloride and 600 ml of THF was cooled to −50° C. under a gas stream of nitrogen. To the mixture, 20.1 g (179.1 mmol) of t-BuOK was added and stirred for 1 hour. To the mixture, a solution of 37.0 g (148.9 mmol) of trans-4-(trans-4-(3-_butenyl)cyclohexyl)cyclohexane carbaldehyde in 400 ml of THF was added dropwise with maintaining the temperature below −50° C. After dropwise addition, the reaction temperature was increased gradually to the room temperature, and stirring was carried out further for 5 hours. The solvent was distilled off under a decresed pressure, 250 ml of water was added and the mixture was extracted with 300 ml of toluene. The organic layer was washed with 200 ml of water for three times and dried with anhydrous magnesium sulphate. The solvent was distilled off under a decreased pressure, and the residue was subjected to silica gel column chromatography (eluent: a mixed solvent of toluene/heptane=3/7), to obtain 16.1 g of crude 1-(2-methoxyethenyl)-trans-4- (trans-4-(3-butenyl) cyclohexyl) cyclohexane.

1. temperaturewith maintaining the temperature below −50° C
2. additionAfter dropwise addition
3. temperaturethe reaction temperature was increased gradually to the room temperature
4. stirringstirring
5. waitwas carried out further for 5 hours
6. distillationThe solvent was distilled off under a decresed pressure, 250 ml of water
7. additionwas added
8. extractionthe mixture was extracted with 300 ml of toluene
9. washThe organic layer was washed with 200 ml of water for three times
10. dry with materialdried with anhydrous magnesium sulphate
11. distillationThe solvent was distilled off under a decreased pressure

ORD record

ord-a0530a279af54064af044b9d054a6632

Source dataset

uspto-grants-2001_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06180027B2