Diethyl Oxalate → HCID 178473081, compound

HRID 1891174Notes

Reaction equation

HRID 1891174 reaction equation
[Na].[O-]CC.[Na+].[CH2:6]([O:13][C:14]1[CH:19]=[C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:17]([CH:28]([CH3:30])[CH3:29])=[CH:16][C:15]=1[C:31](=[O:33])[CH3:32])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:34](OCC)(=[O:40])[C:35]([O:37][CH2:38][CH3:39])=[O:36]>C(O)C>[CH2:38]([O:37][C:35](=[O:36])[C:34]([OH:40])=[CH:32][C:31]([C:15]1[CH:16]=[C:17]([CH:28]([CH3:30])[CH3:29])[C:18]([O:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[CH:19][C:14]=1[O:13][CH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)=[O:33])[CH3:39]

Participants

6

Reactant 4

HCID 7268Diethyl OxalateHCID 2723922Sodium ethoxide2×HCID 5360545SodiumHCID 247733611-(2,4-Bis(benzyloxy)-5-isopropylphenyl)ethanone

Product 1

HCID 178473081HCID 178473081, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Sodium (2.8 eq) was added to ethanol under nitrogen at room temperature and stirred for 25 minutes to generate sodium ethoxide. 1-(2,4-Bis-benzyloxy-5-isopropyl-phenyl)-ethanone (1 eq) was dissolved in further ethanol and added to the sodium ethoxide solution. Diethyl oxalate (1.64 eq) was added and the reaction mixture heated to reflux for 4 hours. The mixture was allowed to cool to room temperature and enough 1MHCl (aq) was added to acidify the reaction mixture, which was then concentrated in vacuo. The resulting gum was partitioned between dichloromethane and brine, and the organic phase was dried over MgSO4, filtered and evaporated in vacuo to give 4-(2,4-Bis-benzyloxy-5-isopropyl-phenyl)-2-hydroxy-4-oxo-but-2-enoic acid ethyl ester as a yellow gum.

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureto reflux for 4 hours
  3. additionenough 1MHCl (aq) was added
  4. concentrationwas then concentrated in vacuo
  5. customThe resulting gum was partitioned between dichloromethane and brine
  6. dry with materialthe organic phase was dried over MgSO4
  7. filtrationfiltered
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-6d7bd1d8685d402db2d9c93b20918e7c
Source dataset
uspto-grants-2013_08
Patent number
US08507480B2

Reaction notes

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