Sodium Cyanide → [1-(4-Bromophenyl)-cyclopentyl]-acetonitrile

HRID 2169270ノート

反応式

HRID 2169270 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:13]OS(C)(=O)=O)[CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[C-:19]#[N:20].[Na+]>CS(C)=O.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:13][C:19]#[N:20])[CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1

参加物

5

反応物 2

HCID 8929Sodium CyanideHCID 86725919Methanesulfonic acid 1-(4-bromophenyl)-cyclopentylmethyl ester

生成物 1

HCID 86725920[1-(4-Bromophenyl)-cyclopentyl]-acetonitrile収率 87.7%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

反応条件

温度
140 °C

実験手順

To a stirred solution of methanesulfonic acid 1-(4-bromophenyl)-cyclopentylmethyl ester (227) (20 g, 60.01 mmol) in dimethyl sulfoxide (100 mL) were added KI (0.99 g, 6.00 mmol) and NaCN (4.41 g, 90.02 mmol). The reaction mixture was then stirred at 140° C. for 5 h. After completion of the reaction, the reaction mixture was diluted with water, extracted with ethyl acetate (2×250 mL) and the organic layer was washed with water and brine. It was then dried over Na2SO4, and concentrated. The crude product was purified by 100-200 silica column chromatography using 5% ethyl acetate in hexane as the eluent to give [1-(4-bromophenyl)-cyclopentyl]-acetonitrile (228) (13.9 g, 87%) as a colorless thick liquid.

後処理

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate (2×250 mL)
  3. washthe organic layer was washed with water and brine
  4. dry with materialIt was then dried over Na2SO4
  5. concentrationconcentrated
  6. customThe crude product was purified by 100-200 silica column chromatography

出典と根拠

ORDレコード
ord-a731bf4a9c0d4741b14e384748a5e865
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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