反应详情

To a solution of 11-allyloxy-3,6,9-trioxaundecanol (83, 2.33 g, 9.94 mmol) in dry THF (40 mL), sodium hydride (0.95 g, 39.8 mmol) is added in several portions under an argon atmosphere. The mixture is stirred for 30 min. A solution of the iodo derivative 45 (3.0 g, 8.28 mmol) in dry THF (10 mL) is added dropwise, and the mixture stirred for 15 h. The reaction is quenched by adding 2 mL of water, and 70% of the amount of THF is evaporated in vacuo. To dilute the mixture, 70 mL of water are added, and the solution extracted with 5 times 50 mL ethyl acetate. The combined organic extracts are dried over MgSO4 and concentrated in vacuo. The yellow oil obtained is purified by flash column chromatography (gradient petrol ether/ethyl acetate 10:1 to 5:1) to give the title product 84 as a pale yellow oil (1.96 g, 4.2 mmol, 51%).

1. stirringthe mixture stirred for 15 h
2. customThe reaction is quenched
3. additionby adding 2 mL of water, and 70% of the amount of THF
4. customis evaporated in vacuo
5. additionTo dilute the mixture, 70 mL of water
6. additionare added
7. extractionthe solution extracted with 5 times 50 mL ethyl acetate
8. dry with materialThe combined organic extracts are dried over MgSO4
9. concentrationconcentrated in vacuo
10. customThe yellow oil obtained
11. customis purified by flash column chromatography (gradient petrol ether/ethyl acetate 10:1 to 5:1)