Water → Ethyl 3-butyl-1-methyl-1H-indole-5-carboxylate

HRID 349002ノート

反応式

HRID 349002 の反応式
[CH2:1]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:12]=2)[NH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[CH3:19]C(C)([O-])C.[K+].IC.O>CS(C)=O>[CH2:1]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:12]=2)[N:7]([CH3:19])[CH:6]=1)[CH2:2][CH2:3][CH3:4]

参加物

6

反応物 4

HCID 962WaterHCID 6328Methyl iodideHCID 21086100ethyl 3-butyl-1H-indole-5-carboxylateHCID 23665647Potassium tert-butoxide

生成物 1

HCID 21086101Ethyl 3-butyl-1-methyl-1H-indole-5-carboxylate収率 46.3%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
50 °C

実験手順

To a mixture of ethyl 3-butyl-1H-indole-5-carboxylate (0.6 g) in methylsulfoxide (10 mL) was added potassium t-butoxide (0.29 g) and iodomethane (2.0 mL). The mixture was stirred at 50° C. for 18H, at which time the mixture was pored into water (50 mL). The solution was extracted with ethyl acetate and the organic extracts washed three times with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. Column chromatography on silica gel (100 mL) using 5% ethyl acetate in hexanes as eluent to give 0.294 g of the title compound: 1H NMR (CDCl3) δ 0.953, 1.44, 1.69, 2.77, 3.76, 4.40, 6.87, 7.26, 7.91, 8.35.

後処理

  1. extractionThe solution was extracted with ethyl acetate
  2. washthe organic extracts washed three times with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-aa76c3f36433495780bceeda6063faa4
出典データセット
uspto-grants-2007_02
特許番号
US07176242B2

反応ノート

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