Pyridine → 1-(5-Formylpentyl)-2-(1-imidazolyl)-3-methylindole

HRID 1719393Notes

Reaction equation

HRID 1719393 reaction equation
O=[Cr](=O)=O.C1C=CC=CN=1.C1C=CC=CN=1.N1C=CC=CC=1.[OH:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][N:30]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:32]([CH3:39])=[C:31]1[N:40]1[CH:44]=[CH:43][N:42]=[CH:41]1>ClCCl.[O-2].[O-2].[O-2].[Cr+6]>[CH:24]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][N:30]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:32]([CH3:39])=[C:31]1[N:40]1[CH:44]=[CH:43][N:42]=[CH:41]1)=[O:23]

Participants

6

Reactant 3

HCID 1049PyridineHCID 88565Trioxobis(pyridine)chromiumHCID 202681751-(6-Hydroxyhexyl)-3-methyl-2-(1-imidazolyl)indole

Product 1

HCID 202681931-(5-Formylpentyl)-2-(1-imidazolyl)-3-methylindole

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of Collins Reagent prepared with chromium trioxide (5.6 g) and pyridine (8.86 g) in dichloromethane (150 ml) at 0°-5° under a nitrogen atmosphere is added all at once 1.8 g of 1-(6-hydroxyhexyl)-3-methyl-2-(1-imidazolyl)-indole in dichloromethane (15 ml). The mixture is stirred for an additional 25 minutes, then filtered through celite. The filtrate is then passed through a silica gel column. The product is eluted from the silica gel with a 1:1 mixture of ethyl acetate:dichloromethane (500 ml). Concentration in vacuo yields 1-(5-formylpentyl)-2-(1-imidazolyl)-3-methylindole.

Workup

  1. filtrationfiltered through celite
  2. washThe product is eluted from the silica gel with a 1:1 mixture of ethyl acetate
  3. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-123b7c81a9474e0094ce892a803583ff
Source dataset
uspto-grants-1985_09
Patent number
US04539410

Reaction notes

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