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

HRID 1619159Notes

Reaction equation

HRID 1619159 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-methoxyacrylateYield 73.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 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 in 10 mL of dichloromethane 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, filtered and concentrated in a vacuum to afford (E)-methyl 2-(2-((2,5-dimethyl-4-propionylphenoxy)methyl)phenyl)-3-methoxyacrylate 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
  4. concentrationconcentrated in a vacuum

Sources & evidence

ORD record
ord-071e2b60f83a49a4aea102ceb87706ae
Source dataset
uspto-grants-2014_07
Patent number
US08772290B2

Reaction notes

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