Reacción #95464

Ecuación de reacción

sodium hydroxide

2-acetyl-2-fluoro-6-(trimethylsilyl)-5-hexynoic acid ethyl ester

sodium ethoxide ethanol

→

2-fluoro-5-hexynoic acid

Rendimiento 101.0%

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.WAITAfter 6 hours
2. 2
   Otrothe solvent was removed by rotary evaporation
3. 3
   Otrothe residual materials partitioned between ethyl ether and dilute hydrochloric acid
4. 4
   SecadoThe organic layer was dried (MgSO4)
5. 5
   Otrothe solvent removed by rotary evaporation
6. 6
   Otroto give an oil which
7. 7
   workup.DISTILLATIONdistilled

Procedimiento

To a solution of 2-acetyl-2-fluoro-6-(trimethylsilyl)-5-hexynoic acid ethyl ester (6.63 g) in ethanol (20 ml) was added 27 ml of 2.65 M sodium ethoxide/ethanol. After 18 hours, 7 ml of 4 N sodium hydroxide was added. After 6 hours, the solvent was removed by rotary evaporation and the residual materials partitioned between ethyl ether and dilute hydrochloric acid. The organic layer was dried (MgSO4) and the solvent removed by rotary evaporation to give an oil which was vacuum distilled to yield 3.2 g of 2-fluoro-5-hexynoic acid; b.p. 118°/14 mmHg.

Fuente