Dimethyl oxalate → Methyl 4-cyclobutyl-2,4-dioxobutanoate

HRID 869053Notes

Reaction equation

HRID 869053 reaction equation
[CH3:1][C:2]([CH:4]1[CH2:7][CH2:6][CH2:5]1)=[O:3].C[O-].[Na+].[C:11](OC)(=[O:16])[C:12]([O:14][CH3:15])=[O:13]>CO>[CH3:15][O:14][C:12](=[O:13])[C:11](=[O:16])[CH2:1][C:2]([CH:4]1[CH2:7][CH2:6][CH2:5]1)=[O:3]

Participants

5

Reactant 3

HCID 11120Dimethyl oxalateHCID 763981-Cyclobutylethan-1-oneHCID 10942334Sodium Methoxide

Product 1

HCID 54775318Methyl 4-cyclobutyl-2,4-dioxobutanoateYield 53.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of cyclobutyl methyl ketone (4 g, 40.8 mmol) in MeOH (60 mL) was added sodium methoxide (3.3 g, 61.2 mmol) at rt. After a 5 min stirring, dimethyl oxalate (4.8 g, 40.8 mmol) was added. The reaction mixture was stirred for 3 h at rt and concentrated. The residue was taked up in diluted HCl and extracted with EtOAc. The organic layers were concentrated. The residue was purified by silica gel column chromatography (hexane/EtOAc, 9:1) to provide 4 g of the title compound. Rf=0.46 (hexane/EtOAc, 1:1); 1H NMR (300 MHz, CDCl3) δ ppm 1.70-2.40 (m, 6H), 3.58 (quintet, 1H), 3.85 (s, 3H), 6.54 (s, 1H), 13.8-15.0 (br. s, 1H).

Workup

  1. stirringThe reaction mixture was stirred for 3 h at rt
  2. concentrationconcentrated
  3. extractionextracted with EtOAc
  4. concentrationThe organic layers were concentrated
  5. customThe residue was purified by silica gel column chromatography (hexane/EtOAc, 9:1)

Sources & evidence

ORD record
ord-76f244b183024b4ba2c9eb75bf05780a
Source dataset
uspto-grants-2015_03
Patent number
US08969341B2

Reaction notes

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