Nitrogen → 4-(2-Methoxy-vinyl)-cyclohexanecarboxylic acid benzyl ester

Temperature

0 °C

NaHMDS (1.0 M in THF) (466 μL, 466 μmol) was added to a solution of methoxymethyltriphenylphosphonium chloride (160 mg, 466 μmol) in tetrahydrofuran (3.88 mL) at 0° C. in an N2 atmosphere, and the mixture was stirred at 0° C. for one hour. A solution of 4-formyl-cyclohexanecarboxylic acid benzyl ester (cis-trans=4:1 mixture) (95.6 mg, 388 μmol) in tetrahydrofuran (2.00 mL) was added dropwise to the reaction solution at 0° C., and the mixture was stirred for 30 minutes. Thereafter, the reaction mixture was stirred at room temperature for 20 hours and quenched with a saturated aqueous ammonium chloride solution (5 mL). H2O (20 mL) was then added, followed by extraction with dichloromethane (50 mL). The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give 4-(2-methoxy-vinyl)-cyclohexanecarboxylic acid benzyl ester (trans-cis=4:1 and E-Z=2:1 mixture) as a yellow oily substance (49.7 mg, 47%).

1. stirringthe mixture was stirred for 30 minutes
2. stirringThereafter, the reaction mixture was stirred at room temperature for 20 hours
3. customquenched with a saturated aqueous ammonium chloride solution (5 mL)
4. additionH2O (20 mL) was then added
5. extractionfollowed by extraction with dichloromethane (50 mL)
6. dry with materialThe organic layer was dried over sodium sulfate
7. concentrationconcentrated under reduced pressure
8. customThe resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate)

ORD record

ord-864dd6523eaa412e80e601183b5d2b5c

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09169254B2