Sodium hydride → HCID 57280327, compound

Participants

Reaction Conditions

Reaction Steps

Trimethyl phosphonoacetate (182 mg, 1.00 mmol) in THF (1.70 mL) was added dropwise (caution—vigorous reaction!) to sodium hydride (60% in oil) (60 mg, 1.50 mmol) in THF (1.70 mL) under an atmosphere of nitrogen at 0° C. The reaction mixture was stirred for 15 minutes at 0° C. and then 4-fluoro-3-nitrobenzaldehyde (169 mg, 1.00 mmol) in THF (0.50 mL) was added. After 1 hour, EtOAc/water was added and the organic layer washed with more water, dried (Na2SO4), and the solvent concentrated in vacuo. The crude product was purified by column chromatography eluting with 33% EtOAc in heptane to give the title compound. Yield: 160 mg, 71%; LC-MS 41.31 min; HPLC Purity: >75%; MS (ES+) m/z not detectable (M+H)

Provenance & Evidence