Cornforth reagent → HCID 20639747, compound

HRID 635000Notes

Reaction equation

HRID 635000 reaction equation
[CH3:1][C:2]([CH3:15])([CH2:8][CH2:9][CH2:10][C:11]([CH3:14])([OH:13])[CH3:12])[CH2:3][CH2:4][CH2:5][CH2:6]O.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=[O:17].[NH+]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[NH+]1C=[CH:35][CH:34]=[CH:33][CH:32]=1>C(Cl)Cl>[OH:13][C:11]([CH3:14])([CH3:12])[CH2:10][CH2:9][CH2:8][C:2]([CH3:15])([CH3:1])[CH2:3][CH2:4][CH2:5]/[CH:6]=[CH:26]/[CH:27]=[C:28]1/[CH2:32][C@@H:33]([OH:17])[CH2:34][CH2:35][C:29]/1=[CH2:30]

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 21261666HCID 21261666, compound

Product 1

HCID 20639747HCID 20639747, compoundYield 44.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

660 mg of 5,5,9-Trimethyl-decane-1,9-diol (3.05 mmol) was oxidized by reaction with 4.36 g of pyridinium-dichromate (3.8 eq.) in 97 ml of CH2Cl2 at room temperature over night. Filtration over a pad of silica gel, removal of the solvent and flash chromatography (SiO2, hexane/ethylacetate=7/3) furnished 452 mg of the title compound as colourless oil.

Workup

  1. filtrationFiltration
  2. customover a pad of silica gel, removal of the solvent and flash chromatography (SiO2, hexane/ethylacetate=7/3)

Sources & evidence

ORD record
ord-59a6c1f8290842d394d9a59e85a295ab
Source dataset
uspto-grants-2001_02
Patent number
US06184422B2

Reaction notes

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