Cornforth reagent → HCID 22319798, compound

HRID 498109Notes

Reaction equation

HRID 498109 reaction equation
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[CH3:22][O:23][CH2:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][CH2:33][CH:34]2[CH2:41][CH2:40][CH2:39][CH:38]([OH:42])[CH2:37][CH2:36][CH2:35]2)=[CH:28][CH:27]=1>ClCCl.CCOCC>[CH3:22][O:23][CH2:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][CH2:33][CH:34]2[CH2:41][CH2:40][CH2:39][C:38](=[O:42])[CH2:37][CH2:36][CH2:35]2)=[CH:28][CH:27]=1

Participants

5

Reactant 2

HCID 2724130Cornforth reagent2×HCID 22319836HCID 22319836, compound

Product 1

HCID 22319798HCID 22319798, compoundYield 93.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

1.65 g of pyridinium dichromate was dissolved in 30 ml of dichloromethane. To the solution was added 0.40 g of 5-[2-(4-methoxymethoxyphenyl)ethyl]-1-cyclooctanol prepared in Reference Example 2. The reaction solution was stirred at room temperature for two hours. To the reaction solution was added another 2.5 g of pyridinium dichromate. The reaction solution was stirred at room temperature overnight. The reaction solution was diluted with 50 ml of ether and purified on Florisil column eluted with ether, to afford 0.37 g of the titled compound as colorless liquid.

Workup

  1. customprepared in Reference Example 2
  2. stirringThe reaction solution was stirred at room temperature overnight
  3. custompurified on Florisil column
  4. washeluted with ether

Sources & evidence

ORD record
ord-130267f451eb42988de7a1fc3c531ea4
Source dataset
uspto-grants-2005_09
Patent number
US06949585B2

Reaction notes

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