1-Bromopropane → Aryl methoxyacrylate derivative 2

HRID 1619161Notes

Reaction equation

HRID 1619161 reaction equation
[OH:1]/[N:2]=[C:3](/[C:6]1[C:27]([CH3:28])=[CH:26][C:9]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2/[C:18](=[CH:23]\[O:24][CH3:25])/[C:19]([O:21][CH3:22])=[O:20])=[C:8]([CH3:29])[CH:7]=1)\[CH2:4][CH3:5].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:36](Br)[CH2:37][CH3:38]>C(#N)C.O>[CH3:29][C:8]1[CH:7]=[C:6](/[C:3](=[N:2]/[O:1][CH2:36][CH2:37][CH3:38])/[CH2:4][CH3:5])[C:27]([CH3:28])=[CH:26][C:9]=1[O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1/[C:18](=[CH:23]\[O:24][CH3:25])/[C:19]([O:21][CH3:22])=[O:20]

Participants

6

Reactant 3

HCID 78401-BromopropaneHCID 10796Cesium carbonateHCID 88531482methyl (E)-2-[2-[[4-[(E)-C-ethyl-N-hydroxycarbonimidoyl]-2,5-dimethylphenoxy]methyl]phenyl]-3-methoxyprop-2-enoate

Product 1

HCID 88531325Aryl methoxyacrylate derivative 2Yield 77%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 0.12 g (0.3 mmol) of (E)-methyl 2-(2-((4-((E)-1-(hydroxyimino)propyl)-2,5-dimethylphenoxy)methyl)phenyl)-3-methoxyacrylate obtained in Step 4 and 0.2 g (0.61 mmol) of cesium carbonate in 10 mL of acetonitrile (CH3CN) was added propyl bromide (0.05 mL, 0.55 mmol), followed by stirring at room temperature for 3 hours. After completion of the reaction, the solvent was removed under reduced pressure and the residue thus obtained was stirred in water (10 mL) and extracted twice with 10 mL of dichloromethane. The organic layer was dried over anhydrous magnesium sulfate and concentrated in a vacuum and the concentrate was purified by silica gel chromatography to afford 0.1 g of (E)-methyl 2-(2-((2,5-dimethyl-4-((E)-1-(propoxyimino)propyl)phenoxy)-methyl)phenyl)-3-methoxyacrylate as a white oil (yield: 77%).

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was removed under reduced pressure
  3. customthe residue thus obtained
  4. extractionextracted twice with 10 mL of dichloromethane
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated in a vacuum
  7. customthe concentrate was purified by silica gel chromatography

Sources & evidence

ORD record
ord-dffd05e324174ed5a96649e52c0bbf44
Source dataset
uspto-grants-2014_07
Patent number
US08772290B2

Reaction notes

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