Diethyl Oxalate → HCID 54803435, compound

HRID 457357Notes

Reaction equation

HRID 457357 reaction equation
[C:1]([O:8][CH2:9][CH3:10])(=[O:7])[C:2]([O:4]CC)=O.[O-]CC.[Na+].[C:15]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:21])[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]>C(O)C>[CH2:9]([O:8][C:1](=[O:7])[C:2](=[O:4])[CH:16]([C:15](=[O:21])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:17][CH2:18][CH2:19][CH3:20])[CH3:10]

Participants

5

Reactant 3

HCID 7268Diethyl OxalateHCID 70337HexanophenoneHCID 2723922Sodium ethoxide

Product 1

HCID 54803435HCID 54803435, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Diethyl oxalate (7.31 g, 0.05 mol) is added to freshly made sodium ethoxide (1.05 eq.) in ethanol. Hexanophenone (8.81 g, 0.05 mol) is added dropwise, and the resulting mixture is stirred at room temperature overnight. After concentration the residue is partitioned between 3N HCl and ethyl acetate, extracted with ethyl acetate. Combined organic layers are washed with brine and dried with anhydrous Na2SO4. Purification by column chromatography with hexane/ethyl acetate gives the product (172).

Workup

  1. concentrationAfter concentration the residue
  2. customis partitioned between 3N HCl and ethyl acetate
  3. extractionextracted with ethyl acetate
  4. washCombined organic layers are washed with brine
  5. dry with materialdried with anhydrous Na2SO4
  6. customPurification by column chromatography with hexane/ethyl acetate

Sources & evidence

ORD record
ord-f1ea22a361764df3b5d710881fffcea4
Source dataset
uspto-grants-2007_03
Patent number
US07186734B2

Reaction notes

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