Pyridine → HCID 13362113, compound

HRID 1633139Notes

Reaction equation

HRID 1633139 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[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][N:30]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[C: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 20441678HCID 20441678, compound

Product 1

HCID 13362113HCID 13362113, 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 1-(6-hydroxyhexyl)-3-methyl-2-(3-pyridyl)-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 the desired 1-(5-formylpentyl)-2-(3-pyridyl)-3-methylindole as a pale yellow oil; NMR (CDCl3) δ9.7 (t, 1H); IR (neat) 2710, 1720 cm-1.

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-58a4dd7769df4b188ee5423fbe576b68
Source dataset
uspto-grants-1984_10
Patent number
US04478842

Reaction notes

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