Methyl iodide → HCID 58292996, compound

Participants

Reaction Conditions

Reaction Steps

2M LDA in THF (1.83 mL, 3.66 mmol) was added dropwise under N2, to a stirred solution of diethyl(4-nitrobenzyl)phosphonate (1.00 g, 3.66 mmol) in THF (10 mL) at −78° C. After 1 hour, iodomethane (0.456 mL, 7.32 mmol) was added dropwise and the mixture stirred at −78° C. for 30 min then allowed to warm to room temperature during 3-4 h. Water (10 mL) was then added slowly followed by EtOAc (20 mL). The layers were separated and the aqueous phase was extracted with EtOAc (3×20 mL). The organic phases were combined, dried (MgSO4), concentrated in vacuo, and the residue purified by chromatography over silica gel eluting with 10% EtOAc in hexanes to afford 180 mg of pure diethyl[1-(4-nitrophenyl)ethyl]phosphonate (yield: 17%) and 680 mg of a mixture of diethyl(4-nitrobenzyl)phosphonate and diethyl[2-(4-nitrophenyl)propan-2-yl]phosphonate.

Provenance & Evidence