反应详情

温度

23 °C

A suspension of 2-(1-fluorononadec-13-en-4,7-diynyl)-4,5-dihydro-4,4-dimethyloxazole (86 mg) in 3 ml of 3 N HCl was refluxed with stirring under argon for 15 min. It was cooled to about 23° C., diluted with 3 ml of water, and extracted three times with ether. The ether extracts were combined, washed with brine, and dried over MgSO4. Concentration of ether at 35° C./35 mmHg gave the crude acid which was purified by flash chromatography on silica gel (8 g, 230-400 mesh). Elution with HOAc-CH3OH--CHCl3 under nitrogen afforded 49 mg (66% yield by weight) of (Z)-2-fluoro-14-eicosene-5,8-diynoic acid as a colorless oil.

1. temperaturewas refluxed
2. extractionextracted three times with ether
3. washwashed with brine
4. dry with materialdried over MgSO4
5. customConcentration of ether at 35° C./35 mmHg gave the crude acid which
6. customwas purified by flash chromatography on silica gel (8 g, 230-400 mesh)
7. washElution with HOAc-CH3OH