Potassium Hydroxide → 4-(6-Ethoxy-benzofuran-3-ylmethoxy)-1H-indole-2-carboxylic acid

HRID 1804792ノート

反応式

HRID 1804792 の反応式
CC[O:3][C:4]([C:6]1[N:7](C(OC(C)(C)C)=O)[C:8]2[C:13]([CH:14]=1)=[C:12]([O:15][CH2:16][C:17]1[C:21]3[CH:22]=[CH:23][C:24]([O:26][CH2:27][CH3:28])=[CH:25][C:20]=3[O:19][CH:18]=1)[CH:11]=[CH:10][CH:9]=2)=[O:5].[OH-].[K+]>C1COCC1.C(O)C.O>[CH2:27]([O:26][C:24]1[CH:23]=[CH:22][C:21]2[C:17]([CH2:16][O:15][C:12]3[CH:11]=[CH:10][CH:9]=[C:8]4[C:13]=3[CH:14]=[C:6]([C:4]([OH:5])=[O:3])[NH:7]4)=[CH:18][O:19][C:20]=2[CH:25]=1)[CH3:28]

参加物

6

反応物 2

HCID 14797Potassium HydroxideHCID 673604314-(6-Ethoxy-benzofuran-3-ylmethoxy)-indole-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester

生成物 1

HCID 591526644-(6-Ethoxy-benzofuran-3-ylmethoxy)-1H-indole-2-carboxylic acid

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
85 °C

実験手順

4-(6-Ethoxy-benzofuran-3-ylmethoxy)-indole-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester (29a) (7.5 g, 15.6 mmol) is dissolved in 150 ml of a 1:1:1 mixture of THF, ethanol and water. And after addition of KOH pellets (4.4 g, 78.2 mmol) the mixture is stirred for 2 h (TLC control) at 85° C. Then the organic solvent is removed under reduced pressure. The residue is cooled to 0° C. and treated with 2M HCl. The crude product is filtered off and dried under high vacuum. The crude product is recrystallized from ethyl acetate.

後処理

  1. customThen the organic solvent is removed under reduced pressure
  2. temperatureThe residue is cooled to 0° C.
  3. additiontreated with 2M HCl
  4. filtrationThe crude product is filtered off
  5. customdried under high vacuum
  6. customThe crude product is recrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-63b8d52de34f413786b7200f714685e3
出典データセット
uspto-grants-2013_01
特許番号
US08354431B2

反応ノート

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