Dichloromethane → HCID 23284535, compound

HRID 368977Notes

Reaction equation

HRID 368977 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.ClCCl.[Cl:15][C:16]1[C:21]([CH:22]([CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)[OH:23])=[CH:20][CH:19]=[CH:18][N:17]=1>CCOCC>[Cl:15][C:16]1[C:21]([C:22]([CH:24]2[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]2)=[O:23])=[CH:20][CH:19]=[CH:18][N:17]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 23284497HCID 23284497, compoundHCID 178418287HCID 178418287, compound2×

Product 1

HCID 23284535HCID 23284535, compoundYield 88.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Pyridinium chlorochromate (20.0 g, 93 mmol) was added to a dichloromethane (200 ml) solution of 2-chloro-α-cyclohexyl-3-pyridinemethanol (17.0 g, 75 mmol), and the mixture was stirred at room temperature for 4 hours. The reaction solution was mixed with pyridinium chlorochromate (10.0 g, 46 mmol) and stirred for 2 hours at room temperature, and then ether was added to the reaction solution to remove insoluble matter by filtration. The solvent was evaporated under a reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane-chloroform) to give 2-chloro-3-cyclohexylcarbonylpyridine (14.9 g, 88%) as an oily material.

Workup

  1. stirringstirred for 2 hours at room temperature
  2. customto remove insoluble matter
  3. filtrationby filtration
  4. customThe solvent was evaporated under a reduced pressure
  5. customthe resulting residue was purified by silica gel column chromatography (hexane-chloroform)

Sources & evidence

ORD record
ord-deb5c6386eef458fbc20b84c21ceb126
Source dataset
uspto-grants-2000_10
Patent number
US06136810

Reaction notes

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