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

HRID 2169247ノート

反応式

HRID 2169247 の反応式
[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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒HCID 8058Hexane溶媒

反応条件

温度
140 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e48da707dc62495581c5c0298152bb75
出典データセット
uspto-grants-2015_06
特許番号
US09045486B2

反応ノート

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