Hexamethylphosphoramide → 6-(5-(t-Butyldimethylsilyloxy)pentan-2-yl)-4-hydroxy-3-propionyl-2-H-pyran-2-one

Participants

Reaction Conditions

Reaction Steps

6-Ethyl-4-hydroxy-3-propionyl-2-H-pyran-2-one (III; 0.5 g; 2.56 mmol) was dissolved in 20 ml anhydrous THF and cooled to 0° C. under argon. To the cooled solution, was added LDA (5.12 ml of 1.5 M in cyclohexane; 7.68 mmol; Aldrich) and the reaction mixture was stirred for 30 min. To the cooled reaction mixture, was added 3-bromopropoxy-t-butyldimethylsilane (0.77 g; 3.07 mmol; Aldrich) and 1 ml HMPA (Aldrich). The reaction mixture was stirred for 30 min at 0° C., quenched with saturated NH4Cl, extracted with 3×20 ml EtOAc, dried with anhydrous Na2SO4, and evaporated to an oil. The product was purified via silica chromatography (10% EtOAc in hexanes).

Provenance & Evidence