반응 #794100

반응 방정식

(carbethoxymethylene)triphenylphosphorane

Ethyl 2-fluoroacetate

diisobutylaluminum hydride

→

ethyl 4-fluorobut-2-enoate

용매

CH2Cl2

CH2Cl2

반응 조건

후처리

1. 1
   온도maintaining the internal temperature below −70° C
2. 2
   기타was allowed to slowly reach room temperature
3. 3
   workup.STIRRINGwhile stirring overnight
4. 4
   기타It was then quenched with methanol
5. 5
   여과filtered
6. 6
   농축concentrated
7. 7
   기타to give the product
8. 8
   workup.ADDITIONas a mixture of isomers (E/Z=3:1)

실험 절차

Ethyl 2-fluoroacetate (21.0 g) in CH2Cl2 (200 mL) at −78° C. was treated dropwise over 45 min with a 1.0 M solution of diisobutylaluminum hydride in CH2Cl2 (200 mL) maintaining the internal temperature below −70° C. Stirring was continued at −78° C. for 30 minutes and then (carbethoxymethylene)triphenylphosphorane (70.0 g) was added in one portion. The reaction mixture was allowed to slowly reach room temperature while stirring overnight. It was then quenched with methanol, filtered and concentrated to give the product as a mixture of isomers (E/Z=3:1).

출처