反应详情

A solution of dimethyl bicyclo[3.3.1]nonane-1,5-dicarboxylate (8.32 g, 36.8 mmol) and Ba(OH)2.8H2O (5.80 g, 18.4 mmol) in ethanol (40 mL) and H2O (10 mL) was refluxed overnight. After cooled to room temperature, the mixture was concentrated under reduced pressure. The resulting residue was added diluted with water (100 mL) and extracted with diethyl ether (3×200 mL). The combined organic layer was washed with brine (100 mL), dried over sodium sulfate and concentrated under reducer pressure to recover starting material as an orange oil. The aqueous phase was adjusted to pH 1˜2 with 2N aq. HCl, and extracted with dichloromethane (3×100 mL). The combined organic layer was washed with brine (100 mL), dried over sodium sulfate and concentrated under reduced pressure to afford 1.8 g (67%) of 5-(methoxycarbonyl)bicyclo[3.3.1]nonane-1-carboxylic acid as a white solid. ESI-MS m/z: 213 (M+H)+.

1. concentrationthe mixture was concentrated under reduced pressure
2. additionThe resulting residue was added
3. additiondiluted with water (100 mL)
4. extractionextracted with diethyl ether (3×200 mL)
5. washThe combined organic layer was washed with brine (100 mL)
6. dry with materialdried over sodium sulfate
7. concentrationconcentrated under reducer pressure
8. customto recover
9. extractionextracted with dichloromethane (3×100 mL)
10. washThe combined organic layer was washed with brine (100 mL)
11. dry with materialdried over sodium sulfate
12. concentrationconcentrated under reduced pressure