Isobutyraldehyde → HCID 131723403, compound

Participants

Reaction Conditions

Reaction Steps

This procedure was adapted from J. Chem. Soc. Perkin Trans. I. 1997, p 771. To a solution of N,N-diisopropylamine (1 mL, 7.69 mmol) in THBF (13 mL) at 0° C. as added n-butyllithium (4.2 mL, 8.46 mmol, 2 M in hexanes). After stirring the mixture for 30 min, it was cooled to −78° C. and 2-tetrahydrofuroic acid, methyl ester (1 g, 7.69 mmol) in THF (13 mL) was added. The reaction mixture was stirred at the same temperature for 15 min and then warmed to −40° C. Isobutyraldehyde (1 mL, 11.5 mmol) was added and stirring was continued for 1 hr and −40° C. The reaction mixture was then warmed to 0° C. and stirred for 1 hr before it was quenched HCl (30 mL, 1M). Extracted with 2×50 mL of ethyl acetate, washed with brine, dried over anhydrous magnesium sulfate. Filtration and evaporation gave the crude product 2.63 g as an oil. Flash column chromatography on silica gel eluted with 15:85 ethyl acetate/hexane gave the desired product (688 mg, 44% yield).

Provenance & Evidence