Pyridine → 3-Methyl-1-(phenylsulfonyl)-2-indoleacetaldehyde

HRID 1657312Notes

Reaction equation

HRID 1657312 reaction equation
N1C=CC=CC=1.[CH3:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)(=[O:19])=[O:18])[C:9]=1[CH2:26][CH2:27][OH:28]>ClCCl.[O-2].[O-2].[O-2].[Cr+6]>[CH3:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)(=[O:19])=[O:18])[C:9]=1[CH2:26][CH:27]=[O:28]

Participants

5

Reactant 2

HCID 1049PyridineHCID 103136112-[3-Methyl-1-(phenylsulfonyl)indol-2-yl]ethanol

Product 1

HCID 104257273-Methyl-1-(phenylsulfonyl)-2-indoleacetaldehydeYield 67.6%

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of chromium trioxide (1.2 g) and pyridine (1.9 g) in dichloromethane was stirred at ambient temperature for 15 minutes, and then 2-[3-methyl-1-(phenylsulfonyl)indol-2-yl]ethanol (630 mg) in dichloromethane [2 ml) was added. The resultant mixture was stirred at room temperature for 15 minutes. The separated organic layer was washed with water and brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was chromatographed over silica gel (eluted with 5% ethyl acetate in toluene) to give 3-methyl-1-(phenylsulfonyl)-2-indole acetaldehyde (423 mg).

Workup

  1. washThe separated organic layer was washed with water and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customevaporated in vacuo
  4. customThe residue was chromatographed over silica gel (eluted with 5% ethyl acetate in toluene)

Sources & evidence

ORD record
ord-90c6748ba12647b685a6c533de62c0c9
Source dataset
uspto-grants-1993_10
Patent number
US05256780

Reaction notes

Loading…