Acetonitrile → 3-Oxo-3-(1-(trifluoromethyl)cyclopropyl)propanenitrile
Reaction equation
[Li+].[CH3:2][CH:3]([N-:5]C(C)C)C.C(=O)=O.CC(C)=O.C[O:17][C:18]([C:20]1([C:23]([F:26])([F:25])[F:24])[CH2:22][CH2:21]1)=O.C(#N)C>C1COCC1>[O:17]=[C:18]([C:20]1([C:23]([F:26])([F:25])[F:24])[CH2:22][CH2:21]1)[CH2:2][C:3]#[N:5]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 22 °C
Procedure
Add 2 M LDA solution in THF (19.15 mL, 38.3 mmol) to a dry ice-acetone cooled solution of 1-trifluoromethyl-cyclopropane-1-carboxylic acid methyl ester (2.93 g, 17.4 mmol) and acetonitrile (1.43 g mL, 34.8 mmol) in THF (30 mL). Stir reaction mixture at −70° C. for 1.5 hours and then allow to warm to 22° C. for 2 hours. Concentrate, add hexanes, and filter to give a yellow solid. Wash with hexanes and treat with diethyl ether (250 mL) then 2 N HCl (150 mL). Extract aq. layer with diethyl ether (4×100 mL). Dry the combined organic phases over sodium sulfate. Removal of solvent provides 3-Oxo-3-(1-trifluoromethyl-cyclopropyl)-propionitrile (2.99 g, 97% yield). MS (ES−): m/z=176.1 [M+H].
Workup
- customreaction mixture at −70° C. for 1.5 hours
- concentrationConcentrate
- additionadd hexanes
- filtrationfilter
- customto give a yellow solid
- washWash with hexanes
- additiontreat with diethyl ether (250 mL)
- dry with materialDry the combined organic phases over sodium sulfate
- customRemoval of solvent
Sources & evidence
- ORD record
- ord-92cb14cae357481587b50a8b36769352
- Source dataset
- uspto-grants-2010_01
- Patent number
- US07652015B2
Reaction notes
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