反应详情

A solution of n-butyllithium (5.70 mL of 1.6 M solution in hexane, 9.12 mmol) was added to 8-(1,3-thiazol-2-yl)-1,4-dioxaspiro[4.5]decan-8-ol (1.00 g, 4.14 mmol) in THF (10 mL) at −78° C. with stirring under N2. After being stirred at −78° C. for 1 h, methyl iodide (0.71 mL, 9.12 mmol) was added to the lithiated compound solution via syringe at −78° C. The reaction mixture was allowed to warm to room temperature slowly and stirred overnight. Water and EtOAc were added. The aqueous layer was extracted with EtOAc (3×). The combined organic layers were washed with saturated NaCl, dried (MgSO4), concentrated and flash chromatographed using 20% EtOAc/hexane to give 0.77 g of the title compound in 71% yield. MS (EI) (M+H)+=256.1.

1. stirringAfter being stirred at −78° C. for 1 h
2. stirringstirred overnight
3. extractionThe aqueous layer was extracted with EtOAc (3×)
4. washThe combined organic layers were washed with saturated NaCl
5. dry with materialdried (MgSO4)
6. concentrationconcentrated
7. customflash chromatographed