反应详情

A solution of 4,4-dimethyl-7-(1-methylene-hexyl)-chroman (0.442 g, 1.71 mmole) in 8 mL of THF at 0° C. was treated with 1.71 mL of 1M BH3.THF complex. The reaction mixture was stirred at room temperature for three hours and then cooled to 0° C. The mixture was treated successively with 0.3 mL of water, 0.34 mL of 3M sodium hydroxide and 0.34 mL of 30% hydrogen peroxide, stirred at room temperature for two hours and then diluted with 10 mL of water. The pH was adjusted to 4.0 with 10% HCl and extracted with three 12.5 mL portions of ether. The combined-organic extracts were dried over MgSO4, filtered and concentrated in vacuo to give a pale yellow oil. The product was purified by flash chromatography (SiO2, 10-20% ethyl acetate in hexanes) to yield 0.366 g of 2-(4,4-dimethyl-chroman-7-yl)-heptan-1-ol as a colorless oil.

1. temperaturecooled to 0° C
2. stirringstirred at room temperature for two hours
3. extractionextracted with three 12.5 mL portions of ether
4. dry with materialThe combined-organic extracts were dried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customto give a pale yellow oil
8. customThe product was purified by flash chromatography (SiO2, 10-20% ethyl acetate in hexanes)