Water → Ethyl 2-(bicyclo[3.2.1]octan-3-ylidene)acetate

Temperature

0 °C

To a suspension of NaH (1.55 g, 38.7 mmol, 60% dispersion in oil) in 1,2-dimethoxy ethane (70 mL) at 0° C., triethyl phosphono acetate (8.38 mL, 41.9 mmol) was added. The resulting mixture was stirred 15 minutes at 0° C., 15 minutes at room temperature, and cooled to 0° C. Then, a solution of bicyclo[3.2.1]octan-3-one (Biogene, 4.0 g, 32.2 mmol) in 1,2-dimethoxy ethane (20 mL) was added and the resulting solution was stirred for 5 minutes at 0° C. and then stirred at room temperature overnight. Water was added and the aqueous layer was extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with H2O (50 mL), brine (50 mL), dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography using an Analogix® Intelliflash280™ (Hex-EtOAc, 0 to 25%) to give the title compound. MS (DCI/NH3) m/z 212 (M+NH4)+

1. temperaturecooled to 0° C
2. stirringthe resulting solution was stirred for 5 minutes at 0° C.
3. stirringstirred at room temperature overnight
4. extractionthe aqueous layer was extracted with ethyl acetate (3×50 mL)
5. washThe combined organic layers were washed with H2O (50 mL), brine (50 mL)
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. customThe residue was purified by flash chromatography

ORD record

ord-ccb359757e2f462a8d4ac6847b39e2e2

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08962639B2