反应详情

Benzyl alcohol (1 molar equivalent) is added dropwise to a stirred suspension of sodium hydride (1 molar equivalent) in dry dimethylformamide maintained at 0° to 5° C. throughout the addition. The reaction mixture is allowed to warm to and then is maintained at room temperature for 1/2 hour. After cooling to 0° to 5° C., the reaction mixture is treated with 1-bromo-4(S)-acetyloxy-2-nonyne (1 molar equivalent) added dropwise over 1/2 hour. The resulting reaction mixture is stirred at ambient temperature for 2 hours and then diluted with water providing a turbid mixture which is extracted with ether. The organic extract is washed with water and saturated aqueous brine, dried over sodium sulfate and filtered. Evaporation (in vacuo at 40° to 50° C.) of the filtrate leaves an oily residue which is distilled to provide the pure title compound.

1. temperaturemaintained at 0° to 5° C. throughout the addition
2. temperatureto warm to and
3. temperatureAfter cooling to 0° to 5° C.
4. additionadded dropwise over 1/2 hour
5. customThe resulting reaction mixture
6. extractionis extracted with ether
7. extractionThe organic extract
8. washis washed with water and saturated aqueous brine
9. dry with materialdried over sodium sulfate
10. filtrationfiltered
11. customEvaporation (in vacuo at 40° to 50° C.) of the filtrate
12. customleaves an oily residue which
13. distillationis distilled