Cyclohexanone, 2-[(phenylmethoxy)methyl]- → (((2-Methylenecyclohexyl)methoxy)methyl)benzene

Temperature

-78 °C

An oven-dried 250 mL one-necked round bottomed flask was charged with methyltriphenylphosphonium bromide (4.3 g, 12.3 mmol) and dry THF (20 mL) and then cooled to −78° C. To this solution was added n-BuLi (2.8 M in hexane, 4.3 mL, 12.3 mmol) over 10 min by syringe. The resultant red ylide solution was then warmed to rt, stirred for 3 hours, and cooled to −78° C. To this ylide solution was added 2-((benzyloxy)methyl)cyclohexanone (1.8 g, 8.6 mmol) in dry THF (5 mL) via syringe over 10 min. After being stirred for 1 hour at −78° C., the reaction mixture was warmed to rt slowly and stirred for 10 hours. After that the reaction mixture was cooled to 0° C., quenched with aq. NaHCO3 (60 mL), and extracted with ether (3×60 mL). The organic layer was washed with brine (60 mL) and dried over sodium sulfate, filtered, and concentrated. The residue was chromatographed with hexane-Et2O isocratic 10% as eluant to give the title compound as clear oil. MS m/z 217.1 (M+1).

1. temperatureThe resultant red ylide solution was then warmed to rt
2. temperaturecooled to −78° C
3. stirringAfter being stirred for 1 hour at −78° C.
4. temperaturethe reaction mixture was warmed to rt slowly
5. stirringstirred for 10 hours
6. temperatureAfter that the reaction mixture was cooled to 0° C.
7. customquenched with aq. NaHCO3 (60 mL)
8. extractionextracted with ether (3×60 mL)
9. washThe organic layer was washed with brine (60 mL)
10. dry with materialdried over sodium sulfate
11. filtrationfiltered
12. concentrationconcentrated
13. customThe residue was chromatographed with hexane-Et2O isocratic 10% as eluant

ORD record

ord-e8199a98ce4740579e234a34828a0066

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09150568B2