Water → 8-(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 (8.1 mL, 12.92 mmol) was added to a solution of thiazole (1.0 g, 11.75 mmol) in THF (10 mL) at −78° C. with stirring under N2. After being stirred at −78° C. for 1 h, a solution of 1,4-cyclohexanedione mono-ethylene ketal (1.84 g, 11.75 mmol) in THF (10 mL) was added to the solution via syringe and stirring was continued for 3 h at −78° C. Water (5 mL) was added, and the reaction mixture was warmed to room temperature and extracted using EtOAc three times. The combined organic layers were dried (MgSO4), filtered, concentrated in vacuo and chromatographed to yield 2.53 g (89%) of the desired compound. MS (M+H)+=242.2.

Provenance & Evidence