Cornforth reagent → HCID 57008461, compound

HRID 1781555Notes

Reaction equation

HRID 1781555 reaction equation
[CH3:1][O:2][C:3]1[C:11]([CH3:12])=[C:10]2[C:6]([C:7](=[O:13])[O:8][CH2:9]2)=[C:5]([O:14][S:15]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)(=[O:17])=[O:16])[C:4]=1[CH2:25][CH:26]=[C:27]([CH3:32])[CH:28]([OH:31])[CH:29]=[CH2:30].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>C(Cl)Cl>[CH3:1][O:2][C:3]1[C:11]([CH3:12])=[C:10]2[C:6]([C:7](=[O:13])[O:8][CH2:9]2)=[C:5]([O:14][S:15]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)(=[O:17])=[O:16])[C:4]=1[CH2:25][CH:26]=[C:27]([CH3:32])[C:28](=[O:31])[CH:29]=[CH2:30]

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 54317759HCID 54317759, compound

Product 1

HCID 57008461HCID 57008461, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The oil product from Example ZC-1B, 6-(1,3-dihydro-6-methoxy -7-methyl-3-oxo-4-p-toluenesulfonyloxy-5-isobenzofuranyl)-3-hydroxy -4-methylhexa-1,4-diene, was dissolved in methylene chloride (20 mL) and 4A molecular sieves (2 g) were added. With vigorous stirring, pyridinium dichromate (2 g) was added and the reaction allowed to proceed for 3 hours. The mixture was then filtered through a celite filled fritted funnel capped with silica gel. Solvent removal was followed by flash chromatography (hexanes/methylene chloride/ether, 4/4/1) to provide the solid product 6-(1,3-dihydro-6-methoxy-7-methyl-3-oxo-4-p-toluenesulfonyloxy -5-isobenzofuranyl)-4-methylhexa-1,4-dien-3-one (0.45 g), which was carried on without further purification.

Workup

  1. filtrationThe mixture was then filtered through a celite
  2. additionfilled fritted funnel
  3. customcapped with silica gel
  4. customSolvent removal

Sources & evidence

ORD record
ord-976750afea43480dbde7862b5dd1dd25
Source dataset
uspto-grants-1997_05
Patent number
US05633279

Reaction notes

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