Hexamethylphosphoramide → HCID 86695810, compound

Participants

Reaction Steps

To 4-hydroxy-6-methyl-3-propionyl-2H-pyran-2-one (XII; 7 g, 38.5 mmol) in 60 ml anhydrous THF at −72° C. under argon, was added freshly prepared LDA (18.5 ml DIPEA in 150 ml THF with 52 ml 2.5 M n-butyllithium, Aldrich) in 150 ml anhydrous THF, and 20 ml HMPA (Aldrich). The reaction mixture was stirred for 1 h. 3-bromopropoxy-t-butyldimethylsilane (7 ml g; 27.7 mmol; Aldrich) in 50 ml anhydrous THF was added over 30 min, and stirred for an additional 5 min. The reaction mixture was quenched with saturated NH4Cl, extracted with 3×150 ml EtOAc, dried with brine and anhydrous Na2SO4, and evaporated to a yellowish oil. The product was purified via silica flash chromatography.

Provenance & Evidence