Lithium Hydroxide → 1-(4-Chlorobenzyl)-1H-indole-2-carboxylic acid

HRID 83596ノート

反応式

HRID 83596 の反応式
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[C:8]2[C:16]([O:18]CC)=[O:17])=[CH:4][CH:3]=1.[OH-].[Li+]>C1COCC1.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[C:8]2[C:16]([OH:18])=[O:17])=[CH:21][CH:22]=1

参加物

5

反応物 2

HCID 3939Lithium HydroxideHCID 10519288Ethyl 1-(4-chlorobenzyl)-1H-indole-2-carboxylate

生成物 1

HCID 223108991-(4-Chlorobenzyl)-1H-indole-2-carboxylic acid

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

Ethyl 1-(4-chlorobenzyl)-1H-indole-2-carboxylate (2.00 g, 6.37 mmol) and lithium hydroxide (1.53 g, 63.7 mmol) were dissolved in THF:water (10 mL: 20 mL). The reaction was heated at 60° C. overnight. The reaction was cooled and further diluted with water. The reaction was transferred into a separatory funnel and was washed with diethyl ether. The aqueous layer was acidified using 2N HCl to pH 2 where a white solid formed. The suspension was returned to the separatory funnel and was washed with ethyl acetate. The organic layer was dried over magnesium sulfate, filtered and concentrated to obtain pure product as a white solid. Yield: 1.47 g, (White solid).

後処理

  1. temperatureThe reaction was cooled
  2. customThe reaction was transferred into a separatory funnel
  3. washwas washed with diethyl ether
  4. customformed
  5. washwas washed with ethyl acetate
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto obtain pure product as a white solid

出典と根拠

ORDレコード
ord-e1e08fd48440426d91aa1e8b93a2939a
出典データセット
uspto-grants-2014_09
特許番号
US08846684B2

反応ノート

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