Ethyl Acetate → [1-(2,5-Dichlorophenyl)-cyclopentyl]-acetonitrile

HRID 2169247Notes

Reaction equation

HRID 2169247 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:9]1([CH2:14]OS(C)(=O)=O)[CH2:13][CH2:12][CH2:11][CH2:10]1.[C-:20]#[N:21].[Na+].C(OCC)(=O)C>CS(C)=O.CCCCCC.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:9]1([CH2:14][C:20]#[N:21])[CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

7

Reactant 3

HCID 8857Ethyl AcetateHCID 8929Sodium CyanideHCID 86725896Methanesulfonic acid 1-(2,5-dichlorophenyl)-cyclopentylmethyl ester

Product 1

HCID 86725897[1-(2,5-Dichlorophenyl)-cyclopentyl]-acetonitrileYield 55.43%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8058HexaneSolvent

Conditions

Temperature
140 °C

Procedure

To a stirred solution of methanesulfonic acid 1-(2,5-dichlorophenyl)-cyclopentylmethyl ester (201) (24 g, 74.53 mmol) in dimethyl sulfoxide (200 mL) KI (1.237 g, 7.453 mmol) and NaCN (5.478 g, 111.801 mmol) were added. The mixture was heated to 140° C. and stirred for 5 h. Silica TLC was performed (10% ethyl acetate in hexane, Rf=0.6). The reaction mixture was cooled to room temperature, diluted with water, extracted with ethyl acetate, washed with brine, dried, concentrated. The obtained crude product was purified using normal silica gel (100-200 mesh) column chromatography using a gradient eluent of 2 to 10% ethyl acetate in hexane to get pure [1-(2,5-dichlorophenyl)-cyclopentyl]-acetonitrile (202) (10.5 g, 55.43%) as a white solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. customdried
  5. concentrationconcentrated
  6. customThe obtained crude product
  7. customwas purified

Sources & evidence

ORD record
ord-e48da707dc62495581c5c0298152bb75
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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