Potassium Iodide → 5-(1H-Indol-3-yl)pentanoic acid cyanomethyl ester

HRID 908939ノート

反応式

HRID 908939 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:24][C:25]#[N:26].[I-].[K+]>CC(C)=O.CN(C)C=O>[C:25]([CH2:24][O:15][C:14](=[O:16])[CH2:13][CH2:12][CH2:11][CH2:10][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][CH:2]=1)#[N:26]

参加物

7

反応物 4

HCID 4875Potassium IodideHCID 7856ChloroacetonitrileHCID 10796Cesium carbonateHCID 123571275-(1H-indol-3-yl)pentanoic acid

生成物 1

HCID 673867685-(1H-Indol-3-yl)pentanoic acid cyanomethyl ester収率 77%

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 6228Dimethylformamide溶媒

実験手順

5-(1H-Indol-3-yl)pentanoic acid (5 g, 23 mmol) was dissolved in a mixture of acetone (25 ml) and dimethylformamide (25 ml), and caesium carbonate (3.75 g, 11.5 mmol), chloroacetonitrile (2.16 ml, 34.5 mmol) and potassium iodide (20 mg) were added in succession. After 6.5 h at 60° C. and 16 h at RT, the solid residues were filtered off and washed with acetone (2×30 ml) and the filtrate was concentrated. The crude product was purified by chromatography on silica gel (130 g) with EA/cyclohexane (1:3). The product was obtained as a colourless solid with an m.p. of 76° C. in a yield of 77% (4.53 g).

後処理

  1. additionwere added in succession
  2. filtration16 h at RT, the solid residues were filtered off
  3. washwashed with acetone (2×30 ml)
  4. concentrationthe filtrate was concentrated
  5. customThe crude product was purified by chromatography on silica gel (130 g) with EA/cyclohexane (1:3)
  6. customThe product was obtained as a colourless solid with an m.p. of 76° C. in a yield of 77% (4.53 g)

出典と根拠

ORDレコード
ord-a61b9df88b1f4fec8b934976358ea9f2
出典データセット
uspto-grants-2011_09
特許番号
US08017630B2

反応ノート

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