反应详情

5.0 mL of lithium diisopropylamide (2M/tetrahydrofuran-ethylbenzene, 10 mmol) was stirred and cooled on dry ice-ethanol bath and 8.0 mL tetrahydrofuran solution containing 0.95 g (4.0 mmol) of 2-(N,N-diethylcarbamoyloxy)-6-methoxytoluene was added dropwise thereto over 16 minutes. After one minute, warming was started under room temperature and after the mixture was stirred for 47 minutes, it was allowed to stand overnight. 10 mL of toluene and 10 mL of water were added thereto and after the mixture was stirred for 4 minutes, it was transferred into a separatory funnel and settled. The aqueous layer was separated and collected and combined with aqueous layers extracted from the organic layer with 2 N potassium hydroxide aqueous solution twice (5.0 mL for each time). After this aqueous layer was washed with 10 mL of toluene, 10 mL of toluene was added therein and 20 mL of 2 N hydrochloric acid aqueous solution was added thereto while being stirred and the mixture was transferred into a separatory funnel and settled. The organic layer was separated and collected and combined with the organic layer extracted from the aqueous layer with 5 mL of toluene. This organic layer was washed with 5 mL of water twice and then concentrated in vacuo, and thereby 0.81 g of the title compound was obtained.

1. temperaturecooled on dry ice-ethanol bath
2. additionwas added dropwise
3. waitAfter one minute
4. temperaturewarming
5. customwas started under room temperature
6. waitto stand overnight
7. stirringafter the mixture was stirred for 4 minutes
8. customit was transferred into a separatory funnel
9. customThe aqueous layer was separated
10. customcollected
11. extractionextracted from the organic layer with 2 N potassium hydroxide aqueous solution twice (5.0 mL for each time)
12. washAfter this aqueous layer was washed with 10 mL of toluene, 10 mL of toluene
13. additionwas added
14. addition20 mL of 2 N hydrochloric acid aqueous solution was added
15. stirringwhile being stirred
16. customthe mixture was transferred into a separatory funnel
17. customThe organic layer was separated
18. customcollected
19. extractionextracted from the aqueous layer with 5 mL of toluene
20. washThis organic layer was washed with 5 mL of water twice
21. concentrationconcentrated in vacuo