Water → (1-Phenylcyclopentyl)acetonitrile

HRID 2169155Notes

Reaction equation

HRID 2169155 reaction equation
[C:1]1([C:7]2([CH2:12]OS(C)(=O)=O)[CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[I-].[K+].[C-:20]#[N:21].[Na+].O>CS(C)=O>[C:1]1([C:7]2([CH2:12][C:20]#[N:21])[CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 4875Potassium IodideHCID 8929Sodium CyanideHCID 19437914(1-Phenylcyclopentyl)methyl methanesulfonate

Product 1

HCID 223258(1-Phenylcyclopentyl)acetonitrileYield 51.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
140 °C

Procedure

To a stirred solution of methanesulfonic acid 1-phenyl-cyclopentylmethyl ester (24-01) (6 g, 23.59 mmol) in dimethyl sulfoxide (18 mL) were added potassium iodide (392 mg, 2.59 mmol) and sodium cyanide (1.734 g, 35.384 mmol). The mixture was stirred for 140° C. for 16 h. After completion of the reaction, water was added and the mixture was filtered through celite. The filtrate was extracted with ethyl acetate, dried and evaporated to get a crude product which was purified using a normal silica column using 15% ethyl acetate in hexane to afford (1-phenyl-cyclopentyl)-acetonitrile (25-01) (2.25 g, 51.4%) as a yellow liquid.

Workup

  1. additionwas added
  2. filtrationthe mixture was filtered through celite
  3. extractionThe filtrate was extracted with ethyl acetate
  4. customdried
  5. customevaporated
  6. customto get a crude product which
  7. customwas purified

Sources & evidence

ORD record
ord-abb4fd949270443bb54aaf95a4d30750
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

Loading…