Cornforth reagent → HCID 86756381, compound

HRID 634999Notes

Reaction equation

HRID 634999 reaction equation
[CH3:1][C:2]([CH3:15])([CH2:8][CH:9]=[CH: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:17][C@@H:26]1[CH2:32]/[C:33](=[CH:34]/[CH:35]=[CH:6]/[CH2:5][CH2:4][CH2:3][C:2]([CH3:15])([CH3:1])[CH2:8][C:9]#[C:10][C:11]([CH3:14])([OH:13])[CH3:12])/[C:29](=[CH2:30])[CH2:28][CH2:27]1

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 54168262HCID 54168262, compound

Product 1

HCID 86756381HCID 86756381, compoundYield 38.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

410 mg of 5,5,9-Trimethyl-dec-7-ene-1,9-diol (1.93 mmol) ) was oxidized by reaction with 2.76 g of pyridinium-dichromate (3.8 eq.) in 61 ml of CH2Cl2 at room temperature over night. Filtration over a pad of Celite, removal of the solvent and flash chromatography (SiO2, hexane/ethylacetate=8/2) furnished 245 mg of the title compound as colourless oil.

Workup

  1. filtrationFiltration
  2. customover a pad of Celite, removal of the solvent and flash chromatography (SiO2, hexane/ethylacetate=8/2)

Sources & evidence

ORD record
ord-e66e902802d94f7785ba6e382b6d91de
Source dataset
uspto-grants-2001_02
Patent number
US06184422B2

Reaction notes

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