Sodium Cyanide → Benzo[b]thiophene-3-acetonitrile

HRID 501208

反応式

HRID 501208 の反応式
[C-:1]#[N:2].[Na+].Cl[CH2:5][C:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[S:8][CH:7]=1>CS(C)=O>[S:8]1[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:6]([CH2:5][C:1]#[N:2])=[CH:7]1

参加物

4

反応物 2

HCID 8929Sodium CyanideHCID 766803-(Chloromethyl)benzo(b)thiophene

生成物 1

HCID 76681Benzo[b]thiophene-3-acetonitrile収率 65.9%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒2 回

実験手順

To a stirred solution of NaCN (1.4 g, 28.5 mmol) in DMSO (8 mL) was added 3-(chloromethyl)-1-benzothiophene (4 gm, 21.9 mmol) in DMSO (6 mL) over 15 min. The reaction mixture was stirred at room temperature for 18 h and then quenched with water and extracted with ether (2×50 mL). The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue obtained was purified by silica gel column chromatography using ethyl acetate-hexane (1:1) to furnish 1-benzothien-3-ylacetonitrile (2.5 g, 65%). 1H NMR (200 MHz, CDCl3): δ 3.69 (s, 2H), 7.25-7.91 (m, 5H).

後処理

  1. customquenched with water
  2. extractionextracted with ether (2×50 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue obtained
  8. customwas purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-9e9a173a102d4360b87ed539b30a777f
出典データセット
uspto-grants-2010_08
特許番号
US07772245B2

関連ノート

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