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

HRID 1804792노트

반응식

HRID 1804792 반응식
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]

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 702Ethanol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
85 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-63b8d52de34f413786b7200f714685e3
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08354431B2

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