Hydrochloric Acid → HCID 54188747, compound

HRID 1067769Notes

Reaction equation

HRID 1067769 reaction equation
[C:1]([O:8][CH2:9][CH3:10])(=[O:7])[C:2]([O:4]CC)=O.[O-]CC.[K+].[CH2:15]([O:22][C:23]1[C:24]([N+:31]([O-:33])=[O:32])=[C:25]([CH3:30])[C:26]([Cl:29])=[CH:27][CH:28]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Cl>C(OCC)C>[CH2:15]([O:22][C:23]1[C:24]([N+:31]([O-:33])=[O:32])=[C:25]([CH2:30][C:2](=[O:4])[C:1]([O:8][CH2:9][CH3:10])=[O:7])[C:26]([Cl:29])=[CH:27][CH:28]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7268Diethyl OxalateHCID 10802515HCID 10802515, compoundHCID 23670592Potassium ethoxide

Product 1

HCID 54188747HCID 54188747, compoundYield 53.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Diethyl oxalate, 1.20 g (7.92 mmol), was added dropwise to a suspension of 0.67 g (7.92 mmol) of potassium ethoxide in diethyl ether (50 ml) at room temperature. Subsequently 2.00 g (7.20 mmol) of 3-benzyloxy-6-chloro-2-nitrotoluene was added to the mixture followed by stirring for 4 hours at room temperature. The reaction solution was poured onto 1N hydrochloric acid and the mixture was extracted twice with diethyl ether. The combined extracts were washed with saturated sodium chloride solution. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The residue was isolated and purified by silica gel column chromatography to give 1.60 g (53.5%) of ethyl (3-benzyloxy-6-chloro-2-nitrophenyl)pyruvate.

Workup

  1. extractionthe mixture was extracted twice with diethyl ether
  2. washThe combined extracts were washed with saturated sodium chloride solution
  3. dry with materialAfter drying over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was isolated
  6. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-b08d6fe72a0548ab8d2327565ca07783
Source dataset
uspto-grants-2001_06
Patent number
US06248772B1

Reaction notes

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