Phosphorus oxychloride → HCID 14482882, compound

Participants

Reaction Steps

6-Bromohexan-1-ol was added dropwise to phosphorusoxy chloride (equimolar) in dichloromethane over 30 minutes under nitrogen. The mixture was stirred at room temperature under nitrogen for 16 hours. The mixture was evaporated, dried under vacuum, then distilled under vacuum, to give the pure 6-bromohexyldichlorophosphate compound. Triethylamine and dichlorophosphate (equimolar) were added dropwise over 2 minutes under nitrogen to 1,3-dihexadecyloxy-2-(hydroxymethyl)-2-methyl propane (0.3×molar amount of dichlorophosphate) in dry diethyl ether. The mixture was heated at 60° C. under nitrogen for 16 hours before triethylamine (same molar amount as dichlorophosphate) and water were added and heating maintained for a further two hours. After cooling, the aqueous layer was removed and the residue evaporated to dryness and azeotroped with benzene (×3). The residue was dissolved in diethylether, filtered and evaporated to give a crude product, which was at least partially purified by silica gel chromatography using chloroform:methanol:25% ammonia (690:270:64). Triphenylphosphine was added to the intermediate thus prepared in dry chloroform. The mixture was heated at 60° C. for 16 hours before it was cooled and the solvents evaporated under reduced pressure. The residue was purified by silica gel chromatography, elusing with chloroform:methanol (3:1) to chloroform:methanol:water (65:25:4). Fractions containing the desired compound were combined and evaporated under reduced pressure to give the desired final compound.

Provenance & Evidence