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

HRID 646513Notes

Reaction equation

HRID 646513 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]([CH2:24][CH:25]([CH3:27])[CH3:26])=[CH:12][C:11]=1[C:28](=[O:30])[CH3:29])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:31](OCC)(=[O:37])[C:32]([O:34][CH2:35][CH3:36])=[O:33].Cl>C(O)C>[CH2:35]([O:34][C:32](=[O:33])[C:31](=[O:37])[CH2:29][C:28]([C:11]1[CH:12]=[C:13]([CH2:24][CH:25]([CH3:26])[CH3:27])[C:14]([O:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[CH:15][C:10]=1[O:9][CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)=[O:30])[CH3:36]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7268Diethyl OxalateHCID 5360545SodiumHCID 247746071-(2,4-Bis-benzyloxy-5-isobutyl-phenyl)-ethanone

Product 1

HCID 592647774-(2,4-Bis-benzyloxy-5-isobutyl-phenyl)-2,4-dioxo-butyric acid ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium (3 eq) was added to ethanol under nitrogen at room temperature and stirred until complete dissolution occured. 1-(2,4-Bis-benzyloxy-5-isobutyl-phenyl)-ethanone (1 eq) was added, followed by diethyl oxalate (1.5 eq) and the reaction mixture heated to reflux for 4 hours. The mixture was allowed to cool to room temperature and acidified with 2M HCl (aq) to give a yellow precipitate of 4-(2,4-Bis-benzyloxy-5-isobutyl-phenyl)-2,4-dioxo-butyric acid ethyl ester, which was obtained by filtration.

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureto reflux for 4 hours

Sources & evidence

ORD record
ord-2a507b4d90ba4d28a83a18a093cd76d7
Source dataset
uspto-grants-2010_04
Patent number
US07705027B2

Reaction notes

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