Hydrochloric Acid → 4-(2,4-Bis-benzyloxy-5-bromo-phenyl)-2,4-dioxo-butyric acid ethyl ester

HRID 1891155Notes

Reaction equation

HRID 1891155 reaction equation
[Na].[CH2:2]([O:9][C:10]1[CH:15]=[C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:13]([Br:24])=[CH:12][C:11]=1[C:25](=[O:27])[CH3:26])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:28](OCC)(=[O:34])[C:29]([O:31][CH2:32][CH3:33])=[O:30].Cl>C(O)C>[CH2:32]([O:31][C:29](=[O:30])[C:28](=[O:34])[CH2:26][C:25]([C:11]1[CH:12]=[C:13]([Br:24])[C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:15][C:10]=1[O:9][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)=[O:27])[CH3:33]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7268Diethyl OxalateHCID 5360545SodiumHCID 247744411-(2,4-Bis-benzyloxy-5-bromo-phenyl)-ethanone

Product 1

HCID 592648154-(2,4-Bis-benzyloxy-5-bromo-phenyl)-2,4-dioxo-butyric acid ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

9.75 g sodium (0.424 mol, 3 eq) were dissolved in 500 ml absolute ethanol (1.5 hours). 58 g of 1-(2,4-Bis-benzyloxy-5-bromo-phenyl)-ethanone (0.141 mol, 1 eq) and 30.98 g diethyl oxalate (0.212 mol, 1.5 eq) were added and the mixture was refluxed for 2 hours. After cooling down, the mixture was poured onto 220 ml of 2N aqueous HCl and the product was extracted into 700 ml dichloromethane. The solvent was removed under reduced pressure and the yellow residue was triturated with 150 ml diethyl ether.

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. temperatureAfter cooling down
  3. extractionthe product was extracted into 700 ml dichloromethane
  4. customThe solvent was removed under reduced pressure
  5. customthe yellow residue was triturated with 150 ml diethyl ether

Sources & evidence

ORD record
ord-a2f2a2af2092419a978c7961f361f153
Source dataset
uspto-grants-2013_08
Patent number
US08507480B2

Reaction notes

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