Water → 8-(5-Methyl-1,3-thiazol-2-yl)-1,4-dioxaspiro[4.5]decan-8-ol

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Reaction Steps

A 1.6 M solution of n-butyllithium in hexanes (5.70 mL, 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 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 three times. The combined organic layers were washed with saturated NaCl, dried (MgSO4), concentrated and flash chromatographed using 20% EtOAc/hexanes to give 0.77 g (71%) of the title compound. MS (M+H)+=256.1.

Provenance & Evidence