Sodium Cyanide → (1-Pyridin-2-yl-cyclopentyl)-acetonitrile
Reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1([CH2:12]OS(C)(=O)=O)[CH2:11][CH2:10][CH2:9][CH2:8]1.[C-:18]#[N:19].[Na+]>CS(C)=O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1([CH2:12][C:18]#[N:19])[CH2:11][CH2:10][CH2:9][CH2:8]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 140 °C
Procedure
To a stirred solution of methanesulfonic acid 1-pyridin-2-yl-cyclopentylmethyl ester (433) (2 g, 7.843 mmol) in dimethyl sulfoxide (15 mL), KI (0.13 g, 0.784 mmol), NaCN (0.769 g, 15.686 mmol) were added and the reaction was subjected to heating at 140° C. for 5 h. The reaction mixture was quenched with ice cold water (50 mL) and extracted with ethyl acetate (2×70 mL). The combined extracts were washed with brine, dried and concentrated. The resulting crude product was purified by normal silica gel (100-200 mesh) column chromatography using 15% ethyl acetate in hexane as eluent to get (1-pyridin-2-yl-cyclopentyl)-acetonitrile (434) (1.2 g, 82%) as a colorless liquid.
Workup
- customThe reaction mixture was quenched with ice cold water (50 mL)
- extractionextracted with ethyl acetate (2×70 mL)
- washThe combined extracts were washed with brine
- customdried
- concentrationconcentrated
- customThe resulting crude product was purified by normal silica gel (100-200 mesh) column chromatography
Sources & evidence
- ORD record
- ord-11e8526af7434962991d2fd8ed533215
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09045486B2
Reaction notes
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