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

HRID 2169247Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2169247
[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

Komponenten

7

Edukt 3

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

Produkt 1

HCID 86725897[1-(2,5-Dichlorophenyl)-cyclopentyl]-acetonitrileAusbeute 55,43 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittelHCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-e48da707dc62495581c5c0298152bb75
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09045486B2

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