Pyridine → HCID 20400820, compound

HRID 1980864Notes

Reaction equation

HRID 1980864 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][C:30]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[N:32]([CH3:39])[C:31]=1[C:40]1[CH:41]=[N:42][CH:43]=[CH:44][CH:45]=1>ClCCl.[O-2].[O-2].[O-2].[Cr+6]>[CH:24]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[N:32]([CH3:39])[C:31]=1[C:40]1[CH:41]=[N:42][CH:43]=[CH:44][CH:45]=1)=[O:23]

Participants

6

Reactant 3

HCID 1049PyridineHCID 88565Trioxobis(pyridine)chromiumHCID 20400806HCID 20400806, compound

Product 1

HCID 20400820HCID 20400820, compound

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, 112 mmol) in dichloromethane (150 ml) at 0°-5° under a nitrogen atmosphere is added all at once 1.8 g of 3-(6-hydroxyhexyl)-1-methyl-2-(3-pyridyl)-indole in dichloromethane (15 ml). The mixture is stirred for an additional 30 minutes, the filtered through celite. The filtrate is then passed through a silica gel column. The product is eluted from the silica gel with a mixture of ethyl acetate:dichloromethane (500 ml). Concentration in vacuo yields 3-(5-formylpentyl)-2-(3-pyridyl)-1-methylindole.

Workup

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

Sources & evidence

ORD record
ord-28452e64f7f748108322073eb0151d10
Source dataset
uspto-grants-1985_04
Patent number
US04511573

Reaction notes

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