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

HRID 1058369Notes

Reaction equation

HRID 1058369 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-7d84555bbfc0414fa5866a1de3ebbb35
Source dataset
uspto-grants-2003_02
Patent number
US06515124B2

Reaction notes

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