反应详情

A suspension of sodium hydride (3.23 g. of a 57 wt. % dispersion in mineral oil, 67 mmoles) in dimethylsulfoxide (117 ml.) was heated under a nitrogen atmosphere at 70° to 75° C. until hydrogen evolution stopped (45 min.). Tetrahydrofuran (88 ml.) was added and the mixture cooled to 0° to 5° C. Trimethylsulfonium iodide (13.67 g., 67 mmoles) was then added in portions, followed by rapid addition of a solution of 1,2-di-O-(n-hexadecyl)-3-O-(3-formylbenzyl)-glycerol (7.0 g., 10.6 mmoles) in tetrahydrofuran (58 ml.). The resulting mixture was stirred for 16 hours at room temperature, poured into water (200 ml.) and extracted with ether (3×180 ml.). The combined ether extract was washed with water (2×100 ml.) and saturated aqueous sodium chloride solution (100 ml.), dried (MgSO4), filtered and evaporated in vacuo to an oil (7.0 g., 98% yield), which was sufficiently pure to be used in the next step.

1. custom(45 min.)
2. temperaturethe mixture cooled to 0° to 5° C
3. extractionextracted with ether (3×180 ml.)
4. extractionThe combined ether extract
5. washwas washed with water (2×100 ml.) and saturated aqueous sodium chloride solution (100 ml.)
6. dry with materialdried (MgSO4)
7. filtrationfiltered
8. customevaporated in vacuo to an oil (7.0 g., 98% yield), which