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

HRID 2169247노트

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HRID 2169247 반응식
[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

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매HCID 8058Hexane용매

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온도
140 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e48da707dc62495581c5c0298152bb75
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09045486B2

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