Diethyl Oxalate → HCID 178473081, compound

HRID 2097289Notes

Reaction equation

HRID 2097289 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 1 MHCl (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 1 MHCl (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-346d0c00f5014fd990b2c1ff9c54eb13
Source dataset
uspto-grants-2013_05
Patent number
US08450310B2

Reaction notes

Loading…