反应详情

3-Dodecyloxy-1-triphenylmethoxy-2-propanol (13.5 g, 0.027 mol) was added dropwise to an ice-cooled suspension of sodium hydride (80%, 1.6 g, 0.054 mol) in 150 mL of tetrahydrofuran under nitrogen. After stirring for 2 h at room temperature, heat was applied (55° C.). 1-Bromodecane (6 g, 0.027 mol) was added dropwise, and heating continued for 6 h. After cooling for 3 h, water was added slowly. Diethyl ether (2×100 mL) was added, and the solution washed with 15% sodium thiosulfite, water, and brine. After drying over sodium sulfate, the ether was removed, and the residue chromatographed with a gradient of hexanes:ethyl acetate (100:0 to 20:1) to give 9 g (52%) of a clear liquid.

1. temperaturecooled
2. temperatureheat
3. custom(55° C.)
4. temperatureheating
5. waitcontinued for 6 h
6. temperatureAfter cooling for 3 h
7. washthe solution washed with 15% sodium thiosulfite, water, and brine
8. dry with materialAfter drying over sodium sulfate
9. customthe ether was removed
10. customthe residue chromatographed with a gradient of hexanes:ethyl acetate (100:0 to 20:1)