Sodium hydride → HCID 19790985, compound

HRID 1655727Notes

Reaction equation

HRID 1655727 reaction equation
C([O:3][C:4](=[O:18])[CH:5]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])C.[H-].[Na+].[CH:21]1[C:26]([C:27]([CH2:29]Br)=[O:28])=[CH:25][CH:24]=[C:23]([Cl:31])[CH:22]=1>CN(C)C=O>[CH2:11]([C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])([CH2:29][C:27]([C:26]1[CH:25]=[CH:24][C:23]([Cl:31])=[CH:22][CH:21]=1)=[O:28])[C:4]([OH:3])=[O:18])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 68303p-Chlorophenacyl bromideHCID 69090Diethyl 2-benzylpropanedioate

Product 1

HCID 19790985HCID 19790985, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

5.0 g (20 mmol) of benzylmalonic acid diethyl ester were added dropwise at room temperature to a suspension of 0.87 g of sodium hydride dispersion (55% in oil) in 20 ml of dimethylformamide. Subsequently, the reaction mixture was stirred at room temperature for 20 minutes and thereafter 4.67 g (20 mmol) of omega-bromo-4-chloroacetophenone in 25 ml of dimethylformamide were added dropwise. After completion of the addition, the deep brown colored reaction mixture was stirred at room temperature overnight and thereafter evaporated in a high vacuum. The residue was dissolved in methylene chloride, washed with water and dried over sodium sulfate. Thereafter, the solvent was evaporated under reduced pressure and the residue, for purification, was chromatographed on silica gel with a 6:1 mixture of hexane and ether, to obtain 5.17 g (64%) of 2-(RS)-benzyl-2-carbethoxy-4-(4-chloro-phenyl)-4-oxobutyric acid as a yellowish solid. MS: 357 (M-OC2H5)+, 311 (M-benzyl)+.

Workup

  1. additionAfter completion of the addition
  2. stirringthe deep brown colored reaction mixture was stirred at room temperature overnight
  3. customevaporated in a high vacuum
  4. dissolutionThe residue was dissolved in methylene chloride
  5. washwashed with water
  6. dry with materialdried over sodium sulfate
  7. customThereafter, the solvent was evaporated under reduced pressure
  8. customthe residue, for purification
  9. customwas chromatographed on silica gel with a 6:1 mixture of hexane and ether

Sources & evidence

ORD record
ord-d810344c15884997a63c1ed8430288c0
Source dataset
uspto-grants-1993_10
Patent number
US05250517

Reaction notes

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