Water → 1-Methyl-3-(1-methylethoxy)-5-(phenylmethoxy)-1H-indole-2-carboxylic acid

HRID 21587

反応式

HRID 21587 の反応式
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:8][CH:9]=2)[C:4]([O:19][CH:20]([CH3:22])[CH3:21])=[C:3]1[C:23]([O:25]C(C)(C)C)=[O:24].[OH-].[Na+].O>COCCO>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:8][CH:9]=2)[C:4]([O:19][CH:20]([CH3:22])[CH3:21])=[C:3]1[C:23]([OH:25])=[O:24]

参加物

5

反応物 3

HCID 962Water2 回HCID 14798Sodium HydroxideHCID 108345245-Benzyloxy-3-isopropoxy-1-methyl-1H-indole-2-carboxylic acid tert-butyl ester

生成物 1

HCID 105690841-Methyl-3-(1-methylethoxy)-5-(phenylmethoxy)-1H-indole-2-carboxylic acid収率 88.4%

試薬・触媒・溶媒 1

HCID 80192-Methoxyethanol溶媒

実験手順

A suspension of 1,1-dimethylethyl 1-methyl-3(1-methylethoxy)-5-(phenylmethoxy)-1H-indole-2-carboxylate (5.6 g, 14 mmol) in 80 mL of 2-methoxyethanol is treated with a solution of 50% aqueous sodium hydroxide (5.0 g, 63 mmol) followed by the addition of 15 mL of water. The mixture is stirred at reflux for 3 hours, then cooled and added to 700 mL of water. The mixture is heated on a hot plate until nearly one phase and filtered hot. The warm filtrate is immediately treated with 50 mL of 4.0N HCl. After cooling to room temperature, followed by 1 hour in an ice bath, the precipitated solid is filtered and washed with 25% methanol in water to give 4.2 g (88%) of product suitable for further synthesis. A sample recrystallized from ethyl acetate-hexane has mp 136° C.-dec.

後処理

  1. temperatureat reflux for 3 hours
  2. temperaturecooled
  3. temperatureThe mixture is heated on a hot plate until nearly one phase
  4. filtrationfiltered hot
  5. additionThe warm filtrate is immediately treated with 50 mL of 4.0N HCl
  6. filtrationthe precipitated solid is filtered
  7. washwashed with 25% methanol in water

出典と根拠

ORDレコード
ord-9619e7daf99446a5b0dceda6fd6203e7
出典データセット
uspto-grants-1995_06
特許番号
US05424329

関連ノート

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