反应详情

To a solution of carbon tetrabromide (27.0 g) in methylene chloride (27 mL) was added dropwise a solution of triphenylphosphine (42.8 g) in methylene chloride (85 mL) at ice temperature. The mixture was stirred at ice temperature for 20 min., and then to the mixture was added dropwise a solution of 3-(2-ethylbutyl)cyclobutanecarbaldehyde in methylene chloride at ice temperature. After stirring at ice temperature for 40 min., saturated aqueous sodium bicarbonate (250 mL) was added dropwise to the mixture. The aqueous layer was removed, and the organic layer was washed with water (50 mL) and brine (50 mL), then dried over sodium sulfate. The sodium sulfate was filtered off and the filtrate was concentrated in vacuo. To the residue were added hexane/chloroform=1/1 (100 mL), silica gel (50 g) and hexane (300 mL). The mixture was filtered and the filtrate was concentrated in vacuo. To the residue was added hexane (300 mL), and the mixture was filtered. The filtrate was concentrated in vacuo. The resultant residue was purified by silica gel column chromatography (Eluent: hexane) to give the title compound (9.78 g).

1. stirringAfter stirring at ice temperature for 40 min.
2. customThe aqueous layer was removed
3. washthe organic layer was washed with water (50 mL) and brine (50 mL)
4. dry with materialdried over sodium sulfate
5. filtrationThe sodium sulfate was filtered off
6. concentrationthe filtrate was concentrated in vacuo
7. additionTo the residue were added hexane/chloroform=1/1 (100 mL), silica gel (50 g) and hexane (300 mL)
8. filtrationThe mixture was filtered
9. concentrationthe filtrate was concentrated in vacuo
10. additionTo the residue was added hexane (300 mL)
11. filtrationthe mixture was filtered
12. concentrationThe filtrate was concentrated in vacuo
13. customThe resultant residue was purified by silica gel column chromatography (Eluent: hexane)