反应详情

LiAlH4 (0.95 g, 25 mmol) was added at −20° C. to the solution of 4-(4-tert-Butylphenyl)-2-methyl-2,3,5,6,7,8-hexahydro-1H-cyclopenta[b]naphthalen-1-one (16.6 g, 50 mmol) in Et2O (150 ml). Resulting mixture was allowed to warm to room temperature and stirred for additional 1 h. Then 5% HCl (100 ml) was added, the resulting mixture was extracted by Et2O (3 times of 50 ml). Combined organic phases were washed by water, dried over MgSO4 and evaporated. Benzene (300 ml) and p-TSA (0.5 g) were added, and resulting solution was refluxed with Dean Stark head (control by TLC, benzene/EtOAc 4:1) within 4 h. Then the resulting solution was washed by water, aq. KHCO3, water, dried over MgSO4, passed through silica gel and evaporated giving 12.8 g (81%) of product.

1. customResulting mixture
2. extractionthe resulting mixture was extracted by Et2O (3 times of 50 ml)
3. washCombined organic phases were washed by water
4. dry with materialdried over MgSO4
5. customevaporated
6. additionBenzene (300 ml) and p-TSA (0.5 g) were added
7. customresulting solution
8. washThen the resulting solution was washed by water, aq. KHCO3, water
9. dry with materialdried over MgSO4
10. customevaporated