Reacción #95462

Ecuación de reacción

2-(1-fluorononadec-13-en-4,7-diynyl)-4,5-dihydro-4,4-dimethyloxazole

CHCl3

water

→

(Z)-2-fluoro-14-eicosene-5,8-diynoic acid

Rendimiento 66.0%

Disolventes

HCl

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas refluxed
2. 2
   Extracciónextracted three times with ether
3. 3
   Lavadowashed with brine
4. 4
   Secadodried over MgSO4
5. 5
   OtroConcentration of ether at 35° C./35 mmHg gave the crude acid which
6. 6
   Otrowas purified by flash chromatography on silica gel (8 g, 230-400 mesh)
7. 7
   LavadoElution with HOAc-CH3OH

Procedimiento

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.

Fuente