Butyl iodide → Methyl 1-butyl-1H-indole-5-carboxylate

HRID 14157

反応式

HRID 14157 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.CC(C)([O-])C.[K+].I[CH2:21][CH2:22][CH2:23][CH3:24]>CS(C)=O>[CH2:21]([N:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1)[CH2:22][CH2:23][CH3:24]

参加物

5

反応物 3

HCID 10962Butyl iodideHCID 2737635methyl 1H-indole-5-carboxylateHCID 23665647Potassium tert-butoxide

生成物 1

HCID 21086133Methyl 1-butyl-1H-indole-5-carboxylate

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

To a mixture of methyl 1H-indole-5-carboxylate (6.0 g) in methylsulfoxide (30 mL) was added potassium t-butoxide (3.88 g). The mixture was stirred at room temperature for 10 minutes at which time 1-iodobutane (1.8 mL) was added. The mixture was stirred at room temperature for 5 h then partitioned between water and methylene chloride. The layers were separated and the organic layer washed three times with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Column chromatography on silica gel (100 mL) using 10% ethyl acetate in hexanes as eluent to give 6.18 g of the title compound: 1H NM (CDCl3) δ 0.923, 1.38, 1.83, 3.9, 4.14, 6.58, 7.15, 7.34, 7.9, 8.39.

後処理

  1. additionwas added
  2. customthen partitioned between water and methylene chloride
  3. customThe layers were separated
  4. washthe organic layer washed three times with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-a47c178ea2044a14a353ff7a1b5f3343
出典データセット
uspto-grants-2010_06
特許番号
US07727997B2

関連ノート

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