Sodium Hydroxide → 1-(ethoxymethyl)-1H-indole-4-carboxylic acid

HRID 1886736ノート

反応式

HRID 1886736 の反応式
[CH2:1]([O:3][CH2:4][N:5]1[C:13]2[CH:12]=[CH:11][CH:10]=[C:9]([C:14]([O:16]C)=[O:15])[C:8]=2[CH:7]=[CH:6]1)[CH3:2].[OH-].[Na+]>CO>[CH2:1]([O:3][CH2:4][N:5]1[C:13]2[CH:12]=[CH:11][CH:10]=[C:9]([C:14]([OH:16])=[O:15])[C:8]=2[CH:7]=[CH:6]1)[CH3:2]

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 67468002methyl 1-(ethoxymethyl)-1H-indole-4-carboxylate

生成物 1

HCID 674641781-(ethoxymethyl)-1H-indole-4-carboxylic acid収率 96.7%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
50 °C

実験手順

To a solution of methyl 1-(ethoxymethyl)-1H-indole-4-carboxylate (135 g, 0.58 mol) in methanol (2 L) is added aqueous sodium hydroxide (68 g, 1.74 mol in 340 mL of H2O). The reaction mixture is stirred at 50° C. for 3 h. The volatiles are removed in vacuo. The residue is acidified with HCl (2 M) until pH=3-4, then extracted with EA (2×700 mL). The combined extracts are washed with aqueous saturated sodium chloride (2×250 mL), dried over anhydrous Na2SO4, and concentrated to yield the title compound (123 g, 96%). MS (m/z): 220 (M+H)+.

後処理

  1. customThe volatiles are removed in vacuo
  2. extractionextracted with EA (2×700 mL)
  3. washThe combined extracts are washed with aqueous saturated sodium chloride (2×250 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-2d76d62db68f425aaad211621a0352d7
出典データセット
uspto-grants-2013_08
特許番号
US08501166B2

反応ノート

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