반응 #216504

반응 방정식

n-Butyllithium

diisopropylamine

ethyl diethylphosphonofluoroacetate

trimethylacetaldehyde

→

ethyl (Z)-2-Fluoro-4,4-dimethylpent-2-enoate

용매

hexane

tetrahydrofuran

tetrahydrofuran

water

반응 조건

후처리

1. 1
   workup.ADDITIONwas added
2. 2
   온도to warm to room temperature over 5 hours
3. 3
   기타the bulk of the solvent was removed under reduced pressure
4. 4
   기타The residue was partitioned between diethyl ether and water
5. 5
   기타The organic phase was separated
6. 6
   세척washed with water, 10% hydrochloric acid solution and brine
7. 7
   건조before drying over anhydrous magnesium sulphate
8. 8
   기타The solvent was removed in vacuo

실험 절차

n-Butyllithium (4.8 ml of a 1.6M solution in hexane) was added to a stirred solution of diisopropylamine (1.1 ml) in tetrahydrofuran (15 ml) at 0° C. under nitrogen. The resulting mixture was maintained at 0° C. for 0.5 hour and then cooled to -70° when a solution of ethyl diethylphosphonofluoroacetate (1.7 g) in tetrahydrofuran (5 ml) was added. After a further 0.5 hour at -70° trimethylacetaldehyde (0.76 ml) was added neat and the resulting mixture was allowed to warm to room temperature over 5 hours. After this time, water (5 ml) was added and the bulk of the solvent was removed under reduced pressure. The residue was partitioned between diethyl ether and water. The organic phase was separated, washed with water, 10% hydrochloric acid solution and brine before drying over anhydrous magnesium sulphate. The solvent was removed in vacuo to leave ethyl (Z)-2-Fluoro-4,4-dimethylpent-2-enoate as a pale green oil (1.0 g).

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