反应详情

温度

-70 °C

To a solution of methyl inden-3-ylacetate (2 g, 10.6 mmol) in dry THF (20 mL) at −70° C. was added dropwise a solution of LDA in THF (25.7 mL, 0.87 M, 2.1 eq.). The resulting orange solution was stirred 30 minutes at −70° C. and then 4-methylthiobenzaldehyde (1.6 mL, 11.7 mmol, 1.1 eq.) was added dropwise. The cooling bath was removed and the reaction mixture was left to warm up to room temperature while a precipitate appeared. The reaction mixture was then quenched with a saturated aqueous solution of ammonium chloride and extracted twice with ethyl acetate. The organic phase was washed twice with iN aqueous HCl, then with brine and dried over MgSO4 and evaporated to dryness. The residue was dissolved in methanol (5 mL) and a solution of benzyltrimethylammonium hydroxide in methanol (Triton B, 1.4 M) (6 mL) was added at room temperature. After 10 minutes the reaction mixture was added to 1N aqueous HCl and extracted with ethyl acetate. The organic layer was treated with etheral diazomethane, dried over MgSO4 and evaporated to dryness. The residue was chromatographed on silica gel eluting with a 95:5 mixture of hexane-ethyl acetate to afford the title compound, as an oil.

1. customThe cooling bath was removed
2. waitthe reaction mixture was left
3. temperatureto warm up to room temperature while a precipitate
4. customThe reaction mixture was then quenched with a saturated aqueous solution of ammonium chloride
5. extractionextracted twice with ethyl acetate
6. washThe organic phase was washed twice with iN aqueous HCl
7. dry with materialwith brine and dried over MgSO4
8. customevaporated to dryness
9. dissolutionThe residue was dissolved in methanol (5 mL)
10. additiona solution of benzyltrimethylammonium hydroxide in methanol (Triton B, 1.4 M) (6 mL) was added at room temperature
11. additionAfter 10 minutes the reaction mixture was added to 1N aqueous HCl
12. extractionextracted with ethyl acetate
13. additionThe organic layer was treated with etheral diazomethane
14. dry with materialdried over MgSO4
15. customevaporated to dryness
16. customThe residue was chromatographed on silica gel eluting with a 95:5 mixture of hexane-ethyl acetate