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Ethylene Glycol → 1h-Indole-1-carboxylic acid,5-(2-methyl-1,3-dioxolan-2-yl)-,1,1-dimethylethyl ester

HRID 2078696
ノート
印刷プレビュー

反応式

HRID 2078696 の反応式
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17](=[O:19])[CH3:18])=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:20](O)[CH2:21][OH:22].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.C([O-])(O)=O.[Na+]>C1C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]3([CH3:18])[O:22][CH2:21][CH2:20][O:19]3)=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 174Ethylene GlycolHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 516892Sodium BicarbonateHCID 57637401tert-Butyl 5-acetyl-1H-indole-1-carboxylate2 回

生成物 1

HCID 576373041h-Indole-1-carboxylic acid,5-(2-methyl-1,3-dioxolan-2-yl)-,1,1-dimethylethyl ester

試薬・触媒・溶媒 1

HCID 241
Benzene
溶媒

実験手順

A mixture of 5-acetyl-indole-1-carboxylic acid tert-butyl ester [4.85 g, 18.70 mmol, Intermediate (18)], ethylene glycol (5.0 g), pyridinium p-toluenesulfonate (100 mg) in benzene (35 mL) is refluxed under N2 with a Dean-Stark trap for 24 hours. To this resulting dark reaction mixture is added solid NaHCO3 (2.5 g). After stirring for 15 minutes, it is filtered under suction and washed three times with ethyl acetate (30 mL). The filtrate is washed twice with water (10 mL) and dried over sodium sulfate. The crude is chromatographed on 10 g silica gel cartridge (heptane then 10% ethyl acetate in heptane) afforded 5-(2-methyl-[1,3]dioxolan-2-yl)-indole-1-carboxylic acid tert-butyl ester [Intermediate (19)] as colorless oil; 1H NMR (CDCl3): δ 8.128 (1H, d), 7.706 (1H, s), 7.625 (1H), 7.475 (1H, dd), 6.591 (1H, d), 4.106 (2H, m), 3.843 (2H, m), 1.742 (3H, s), 1.703 (9H, s); LC/MS: 304 (M+H).

後処理

  1. temperatureis refluxed under N2 with a Dean-Stark trap for 24 hours
  2. customTo this resulting dark reaction mixture
  3. filtrationit is filtered under suction
  4. washwashed three times with ethyl acetate (30 mL)
  5. washThe filtrate is washed twice with water (10 mL)
  6. dry with materialdried over sodium sulfate
  7. customThe crude is chromatographed on 10 g silica gel cartridge (heptane

出典と根拠

ORDレコード
ord-fdfd7409e9f04fe291d44d943669075a
出典データセット
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07928231B2

反応ノート

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