Water → 8-Hydroxy-8-(5-thiazolyl)-1,4-dioxaspiro[4.5]decane

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Reaction Steps

A solution of 2-trimethylsilyl-thiazole (2.5 g, 15.89 mmol) in THF (20 mL) was added to a 1.6 M solution of n-butyllithium in hexanes (11.9 mL, 19.07 mmol) at −78° C. with stirring under N2. After being stirred at −78° C. for 0.5 h, a solution of 1,4-cyclohexanedione mono-ethylene ketal (2.48 g, 15.89 mmol) in THF (20 mL) was added to the solution via syringe and stirring was continued for 1 h at −78° C. Water (5 mL) and EtOAc were added, and the reaction mixture was warmed to room temperature and extracted with EtOAc three times. The combined organic layers were dried (MgSO4), filtered, and crystallized from EtOAc to yield 3.4 g (90%) of the desired product. MS (M+H)+=242.1.

Provenance & Evidence