Water → 3-(5-Benzyloxy-indol-1-yl)-hexanoic acid ethyl ester

HRID 1295136

反応式

HRID 1295136 の反応式
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:20]([O:22][C:23](=[O:30])[CH2:24][CH:25](Br)[CH2:26][CH2:27][CH3:28])[CH3:21].O>CN(C=O)C>[CH2:20]([O:22][C:23](=[O:30])[CH2:24][CH:25]([N:14]1[C:15]2[C:11](=[CH:10][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:17][CH:16]=2)[CH:12]=[CH:13]1)[CH2:26][CH2:27][CH3:28])[CH3:21]

参加物

6

反応物 4

HCID 962WaterHCID 146245-BenzyloxyindoleHCID 24758Sodium hydrideHCID 22570372Ethyl-beta-bromocaproate

生成物 1

HCID 674280143-(5-Benzyloxy-indol-1-yl)-hexanoic acid ethyl ester収率 40%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒3 回

実験手順

A solution of 5-benzyloxyindole (5.00 g, 22.4 mmol) in DMF (20 mL) was added dropwise to a stirred solution of sodium hydride (0.91 g, 38.1 mmol) in DMF (50 mL) at 0° C. and stirred for 20 minutes. Ethyl-β-bromocaproate (5.59 g, 26.9 mmol) in DMF (20 mL) was added and the reaction was stirred at room temperature overnight. The reaction was then poured into cold H2O (150 mL) and extracted with ethyl acetate (3×50 mL), dried over magnesium sulfate and concentrated. The residue was purified by flash chromatography on silica gel (40% ethyl acetate in hexane) to give the title compound as oil (40% yield). 1H NNR (CDCl3) δ 7.47 (d, 2H, J=7.2 Hz), 7.38 (t, 2H, J=7.1 Hz), 7.32 (d, 2H, J=8.8 Hz), 7.12 (dd, 2H, J=2.4, 13.7 Hz), 6.94 (dd, 1H, J=2.4, 10.2 Hz), 6.44 (d, 1H, J=3.1 Hz), 5.09 (s, 2H), 4.79 (m, 1H), 3.98 (q, 2H, J=7.1 Hz), 2.80 (m, 2H), 1.90 (m, 2H), 1.25 (m, 2H), 1.07 (t, 3H, J=7.2 Hz), 0.86 (t, 3H, J=7.3 Hz).

後処理

  1. stirringthe reaction was stirred at room temperature overnight
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography on silica gel (40% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-9b52a82b98b844b2a5926778bc48e817
出典データセット
uspto-grants-2007_07
特許番号
US07241789B2

関連ノート

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