Sodium hydride → HCID 58929474, compound

Participants

Reaction Steps

Dimethylphosphite (5.0 g, 45 mmol) was cautiously added to a suspension of NaH (60% dispersion, 2.0 g, 50 mmol) in DMF (45 mL) at 0°. After 2 h, 3-phenoxy propylbromide (10.75 g, 50 mmol) was added, and the mixture stirred at rt for 48 h. The solvent was removed under reduced pressure, the residue dissolved in water (100 mL), extracted with Et2O, and the combined extracts washed with water, brine and dried (MgSO4). The solution was concentrated at reduced pressure to give 10.28 g of crude product. A portion of the crude material (5 g) was distilled to afford 52 (3.4 g, 63%) as a colourless oil. 13C NMR (CDCl3) δ 21.4 (d, J=141.8 Hz), 22.7 (d, J=4.5 Hz), 52.5 (d, J=6.8 Hz), 67.2 (d, J=15 Hz), 114.6, 121.0, 129.6, 158.8. ESMS 245 (M+H)+.

Provenance & Evidence