Water → Ethyl (bicyclo[3.2.0]heptan-6-ylidene)acetate
Reaction equation
[H-].[Na+].[CH:3]12[CH2:9][C:8](=O)[CH:7]1[CH2:6][CH2:5][CH2:4]2.[OH2:11].[O:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1>>[CH:3]12[CH2:9][C:8](=[CH:14][C:13]([O:12][CH2:16][CH3:15])=[O:11])[CH:7]1[CH2:6][CH2:5][CH2:4]2Participants
Procedure
Triethylphosphonoacetate (96.2 g; 429 mmol) was added to a suspension of 60% sodium hydride dispersion (16.5 g; 413 mmol) in tetrahydrofuran (480 mL) maintaining the temperature between 1–4° C. A solution of bicyclo[3.2.0]heptan-6-one (35.0 g; 318 mmol) in tetrahydrofuran (320 ml) was added maintaining the temperature between 5–15° C. The reaction mixture was stirred at ambient temperature overnight. Demineralised water (350 mL) added and the product was extracted with diethyl ether (3×450 ml). The combined organic phases were washed with brine (300 ml), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to leave a pale orange oil. This was purified by chromatography on a silica pad, eluting with 1:19 ethyl acetate:n-hexane. The product containing fractions were combined and concentrated in vacuo to yield the title compound as a colourless oil (47.8 g).
Workup
- temperaturemaintaining the temperature between 1–4° C
- temperaturemaintaining the temperature between 5–15° C
- extractionthe product was extracted with diethyl ether (3×450 ml)
- washThe combined organic phases were washed with brine (300 ml)
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customto leave a pale orange oil
- customThis was purified by chromatography on a silica pad
- washeluting with 1:19 ethyl acetate
- additionThe product containing fractions
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-afeba55eb13c4e29bfd5949d4bd31f21
- Source dataset
- uspto-grants-2006_03
- Patent number
- US07018818B2
Reaction notes
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