Sodium hydride → HCID 131722971, compound

HRID 428805Notes

Reaction equation

HRID 428805 reaction equation
[CH2:1]([O:3][N:4]=[C:5]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH:17]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)[CH3:18])=[CH:12][CH:11]=1)[C:6](=[N:8][OH:9])[CH3:7])[CH3:2].[H-].[Na+].[CH3:28][O:29][C:30](=[O:43])[C:31]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[CH2:41]Br)=[CH:32][O:33][CH3:34]>CN(C)C=O>[CH3:28][O:29][C:30](=[O:43])[C:31]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[CH2:41][O:9][N:8]=[C:6]([CH3:7])[C:5](=[N:4][O:3][CH2:1][CH3:2])[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH:17]([C:19]2[CH:20]=[CH:21][C:22]([Cl:25])=[CH:23][CH:24]=2)[CH3:18])=[CH:12][CH:11]=1)=[CH:32][O:33][CH3:34]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 53395349Methyl 2-[2-(bromomethyl)phenyl]-3-methoxyprop-2-enoateHCID 136016119HCID 136016119, compound

Product 1

HCID 131722971HCID 131722971, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

7 g of 1-[4-(1-{4-chlorophenyl)-ethoxy}-phenyl]-1,2-propanedione-[ethyloxime]-2-oxime dissolved in 25 ml of N,N-dimethylformamide are added dropwise to a suspension of 0.9 g of sodium hydride (55% in oil) in 40 ml of N,N-dimethylformamide and the reaction mixture is then stirred for 10 minutes at room temperature. 5.5 g of 2-(bromomethyl)-α-(methoxymethylene)-phenylacetic acid methyl ester in 20 ml of N,N-dimethylformamide are then added dropwise and the reaction mixture is stirred for a further 1 hour at room temperature. The mixture is then rendered acidic with acetic acid and concentrated by evaporation in vacuo. The residue is dissolved in ethyl acetate and the solution is washed three times with water and once with saturated sodium chloride solution, dried with sodium sulfate and concentrated by evaporation in vacuo. Purification by flash chromatography (silica gel, ethyl acetate/hexane 1:3) yields the E isomer of the title compound having a melting point of 107-109° C. (compound 1-4.2).

Workup

  1. stirringthe reaction mixture is stirred for a further 1 hour at room temperature
  2. concentrationrendered acidic with acetic acid and concentrated by evaporation in vacuo
  3. dissolutionThe residue is dissolved in ethyl acetate
  4. washthe solution is washed three times with water
  5. dry with materialonce with saturated sodium chloride solution, dried with sodium sulfate
  6. concentrationconcentrated by evaporation in vacuo
  7. customPurification by flash chromatography (silica gel, ethyl acetate/hexane 1:3)

Sources & evidence

ORD record
ord-5b604c84833641e0a0b1b22b7821c4f4
Source dataset
uspto-grants-2001_11
Patent number
US06313344B1

Reaction notes

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