Water → HCID 86591249, compound

HRID 584897Notes

Reaction equation

HRID 584897 reaction equation
[H-].[Na+].[CH3:3][CH2:4][O:5][C:6]([CH:8](P(OCC)(OCC)=O)[CH3:9])=[O:7].[CH:18]([C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([CH2:32][N:33](C)[C:34](=[O:41])[C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH:27]=2)=[CH:22][CH:21]=1)=O.O>C1COCC1>[CH3:9]/[C:8](=[CH:18]\[C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([CH2:32][NH:33][C:34]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[O:41])[CH:27]=2)=[CH:22][CH:21]=1)/[C:6]([O:5][CH2:4][CH3:3])=[O:7]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 107155Triethyl 2-phosphonopropionateHCID 22341491N-(4'-formylbiphenyl-3-ylmethyl)-N-methylbenzamide

Product 1

HCID 86591249HCID 86591249, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

440 mg (11 mmol) of sodium hydride (80% in oil) and 10 ml of THF are introduced into a three-necked flask under a stream of nitrogen. A solution of 2.2 ml of triethyl 2-phosphonopropionate in 10 ml of THF is added dropwise, followed by a solution of 3 g (9.1 mmol) of N-(4′-formylbiphenyl-3-ylmethyl)-N-methylbenzamide (prepared in Example 1(e)), and the mixture is stirred at room temperature for 3 hours. The reaction medium is poured into water and extracted with dichloromethane, and the organic phase is separated out after settling of the phases has taken place, dried over magnesium sulfate and evaporated. The residue obtained is purified by chromatography on a column of silica eluded with a mixture of heptane and ethyl acetate (70/30). After evaporation of the solvents, 3 g (80%) of ethyl (E)-2-methyl-3-(3′-{[(1-phenyl-methanoyl)amino]methyl}biphenyl-4-yl)acrylate are collected in the form of an oil.

Workup

  1. extractionextracted with dichloromethane
  2. customthe organic phase is separated out
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue obtained
  6. customis purified by chromatography on a column of silica
  7. additioneluded with a mixture of heptane and ethyl acetate (70/30)
  8. customAfter evaporation of the solvents, 3 g (80%) of ethyl (E)-2-methyl-3-(3′-{[(1-phenyl-methanoyl)amino]methyl}biphenyl-4-yl)acrylate
  9. customare collected in the form of an oil

Sources & evidence

ORD record
ord-82ab8673b0b448ddbfd2b027c6a35270
Source dataset
uspto-grants-2005_08
Patent number
US06927228B2

Reaction notes

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