Methanol → 5-(2-hydroxyethoxy)-1H-indole-2-carboxylic acid

HRID 1874948노트

반응식

HRID 1874948 반응식
CO.[CH3:3][C:4]([Si:7]([CH3:34])([CH3:33])[O:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[N:17](C(OCCC(C)(C)C)=O)[C:16]([C:30]([O-:32])=[O:31])=[CH:15]2)([CH3:6])[CH3:5].[Li+].[OH-]>C1COCC1>[OH:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:16]([C:30]([OH:32])=[O:31])=[CH:15]2.[CH3:6][C:4]([Si:7]([CH3:34])([CH3:33])[O:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:16]([C:30]([OH:32])=[O:31])=[CH:15]2)([CH3:3])[CH3:5]

참가 물질

6

반응물 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 86761647HCID 86761647, 화합물

생성물 2

HCID 184556225-(2-hydroxyethoxy)-1H-indole-2-carboxylic acid수율 16%HCID 68485440HCID 68485440, 화합물수율 7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
70 °C

실험 절차

A methanol solution of 1-(1,1-dimethylethyl)2-ethyl 5-[(2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}ethyl)oxy]-1H-indole-1,2-dicarboxylate (0.200 g, 0.431 mmol) was treated with 1 N LiOH (4 mL). A precipitate formed and THF was added to redissolve the material. The reaction was heated to 70° C. until the starting material was consumed, partitioned between EtOAc and water and the layers separated. The basic aqueous layer was acidified with conc. HCl and extracted with EtOAc. Purification was accomplished by silica gel column chromatography (0-100% EtOAc/hexanes, striped with MeOH) to afford the title compound (0.015 g, 16%) and 5-[(2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}ethyl)oxy]-1H-indole-2-carboxylic acid (0.0114 g, 7%) 1H NMR (400 MHz, Acetone-d6) δ ppm 10.73 (br. s., 1H), 7.43 (d, 1H), 7.15 (d, 1H), 7.10 (d, 1H), 6.96 (dd, 1H), 4.07 (t, 2H), 3.88 (t, 2H).

후처리

  1. customA precipitate formed
  2. dissolutionto redissolve the material
  3. customwas consumed
  4. custompartitioned between EtOAc and water
  5. customthe layers separated
  6. extractionextracted with EtOAc
  7. customPurification

출처 및 근거

ORD 기록
ord-45ac2a52a60e41f3bce3c4b49340bdf9
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08304419B2

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