Cornforth reagent → (E)-methyl 2-(2-((2,5-dimethyl-4-propionylphenoxy)methyl)phenyl)-3-methoxyacrylate

HRID 1619174Notes

Reaction equation

HRID 1619174 reaction equation
[OH:1][CH:2]([C:5]1[C:26]([CH3:27])=[CH:25][C:8]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2/[C:17](=[CH:22]\[O:23][CH3:24])/[C:18]([O:20][CH3:21])=[O:19])=[C:7]([CH3:28])[CH:6]=1)[CH2:3][CH3:4].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>ClCCl>[CH3:28][C:7]1[CH:6]=[C:5]([C:2](=[O:1])[CH2:3][CH3:4])[C:26]([CH3:27])=[CH:25][C:8]=1[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1/[C:17](=[CH:22]\[O:23][CH3:24])/[C:18]([O:20][CH3:21])=[O:19]

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 67954688(E)-methyl 2-(2-((4-(1-hydroxypropyl)-2,5-dimethylphenoxy)methyl)phenyl)-3-methoxyacrylate

Product 1

HCID 67955272(E)-methyl 2-(2-((2,5-dimethyl-4-propionylphenoxy)methyl)phenyl)-3-methoxyacrylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 10 mL of dichloromethane, 0.15 g (0.39 mmol) of (E)-methyl 2-(2-((4-(1-hydroxypropyl)-2,5-dimethylphenoxy)methyl)phenyl)-3-methoxyacrylate obtained in Step 2 was reacted with 0.29 g (0.78 mmol) of pyridinium dichromate at room temperature for 2 hours with stirring, followed by filtration through celite. The organic layer was dried over anhydrous magnesium sulfate and filtered after which the solvent was removed by concentration in a vacuum. (E)-methyl 2-(2-((2,5-dimethyl-4-propionylphenoxy)methyl)phenyl)-3-methoxyacrylate was obtained as a brown oil (0.11 g, yield: 71%).

Workup

  1. filtrationfollowed by filtration through celite
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered after which the solvent
  4. customwas removed by concentration in a vacuum

Sources & evidence

ORD record
ord-8e9b162b79b54b03a1e1aaa1a018a20a
Source dataset
uspto-grants-2014_07
Patent number
US08772290B2

Reaction notes

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