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

HRID 1874948ノート

反応式

HRID 1874948 の反応式
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]

参加物

6

反応物 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 86761647HCID 86761647、化合物

生成物 2

HCID 184556225-(2-hydroxyethoxy)-1H-indole-2-carboxylic acid収率 16%HCID 68485440HCID 68485440、化合物収率 7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
70 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-45ac2a52a60e41f3bce3c4b49340bdf9
出典データセット
uspto-grants-2012_11
特許番号
US08304419B2

反応ノート

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