반응 #816775

반응 방정식

LDA

dry ice acetone

1-methoxy-cyclopropanecarboxylic acid methyl ester

acetonitrile

→

3-(1-Methoxy-cyclopropyl)-3-oxo-propionitrile

수율 96.0%

용매

THF

THF

반응 조건

후처리

1. 1
   workup.WAITat 22° C. for 0.5 hour
2. 2
   기타Evaporate the solvent
3. 3
   기타to give a brown solid
4. 4
   여과Filter
5. 5
   세척wash with hexanes
6. 6
   workup.ADDITIONAdd 2N hydrochloric acid
7. 7
   추출extract three times with diethyl ether (50 mL each)
8. 8
   건조Dry the combined organic phases over sodium sulfate
9. 9
   기타Removal of solvent
10. 10
    기타provides a red oil (3.55 g, 96% yield, ES+(m/z) 140.1 [M+H])

실험 절차

Add a solution of 2 M LDA in THF (29.1 mL, 58.3 mmol) to a dry ice-acetone cooled solution of 1-methoxy-cyclopropanecarboxylic acid methyl ester (WO2005/014577) (3.45 g, 26.5 mmol) and acetonitrile (2.17 g mL, 53.0 mmol) in THF (30 mL). Stir the reaction mixture at −78° C. for 1 hour and then at 22° C. for 0.5 hour. Evaporate the solvent to give a brown solid. Filter and wash with hexanes. Add 2N hydrochloric acid and extract three times with diethyl ether (50 mL each). Dry the combined organic phases over sodium sulfate. Removal of solvent provides a red oil (3.55 g, 96% yield, ES+(m/z) 140.1 [M+H]).

출처