Water → Tert-butyl 6-formyl-1H-indole-1-carboxylate

HRID 1058369ノート

反応式

HRID 1058369 の反応式
[OH:1][CH2:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[CH:8][N:9]2[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[CH:5][CH:4]=1.I(C1C=CC=CC=1C(O)=O)(=O)=O.O>CS(C)=O>[CH:2]([C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[CH:8][N:9]2[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[CH:5][CH:4]=1)=[O:1]

参加物

5

反応物 3

HCID 962WaterHCID 1087942-Iodoxybenzoic acidHCID 23560816tert-Butyl 6-(hydroxymethyl)-1H-indole-1-carboxylate

生成物 1

HCID 14616867Tert-butyl 6-formyl-1H-indole-1-carboxylate収率 42.4%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

A solution of 6-hydroxymethyl-1H-indole-1-carboxylic acid, 1,1-dimethylethyl ester (Example 31; 5.10 g, 20.6 mmol) and o-iodoxybenzoic acid (prepared by the literature procedure: Frigerio, M.; Santagostino, M. Tetrahedron Lett. 1994, 35, 8019-8022; 8.00 g, 28.6 mmol) in dimethylsulfoxide (25 mL) was stirred at room temperature for 4 h. Water (200 mL) was added and the solution was extracted with dichloromethane (3×100 mL). The combined extracts were washed with brine (200 mL), dried (MgSO4), filtered, evaporated in vacuo. The residual material was chromatographed over silica gel (20-30% ethyl acetate/hexanes) to give 6-formyl-1H-indole-1-carboxylic acid, 1,1-dimethylethyl ester (2.14 g, 42% yield) as a colorless solid.

後処理

  1. extractionthe solution was extracted with dichloromethane (3×100 mL)
  2. washThe combined extracts were washed with brine (200 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residual material was chromatographed over silica gel (20-30% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-7d84555bbfc0414fa5866a1de3ebbb35
出典データセット
uspto-grants-2003_02
特許番号
US06515124B2

反応ノート

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