Diethyl Oxalate → 2,4-Diketo4-(4-methyloxazol-5-yl)butyric acid ethyl ester

HRID 129839Notes

Reaction equation

HRID 129839 reaction equation
[C:1]([O:8][CH2:9][CH3:10])(=[O:7])[C:2]([O:4]CC)=O.[C:11]([C:14]1[O:18][CH:17]=[N:16][C:15]=1[CH3:19])(=[O:13])[CH3:12]>[O-]CC.[Na+]>[CH2:9]([O:8][C:1](=[O:7])[C:2](=[O:4])[CH2:12][C:11](=[O:13])[C:14]1[O:18][CH:17]=[N:16][C:15]=1[CH3:19])[CH3:10]

Participants

4

Reactant 2

HCID 7268Diethyl OxalateHCID 110298391-(4-Methyloxazol-5-yl)ethanone

Product 1

HCID 510589382,4-Diketo4-(4-methyloxazol-5-yl)butyric acid ethyl esterYield 78.4%

Reagents, catalysts & solvents 1

HCID 2723922Sodium ethoxideSolvent

Procedure

To a sodium ethoxide solution (2.7 g of sodium and 50 ml of ethanol), a mixture of diethyl oxalate (14.48 g) and 5-acetyl-4-methyloxazole (12.4 g) was added dropwise at 0° C. The resulting mixture as stirred at room temperature for 1.5 hours, and concentrated. The residue was treated with 150 ml of water, and neutralized with 6N HCl. The resulting mixture was filtered to afford 17.5 g of 2,4-diketo-4-(4-methyloxazol-5-yl)butyric acid ethyl ester as white solids. NMR: 1.41 (t, 3H), 2.60 (s, 3H, oxazolyl methyl), 4.40 (q, 2H), 6.93 (s, 1H), 7.99 (s, 1H, 2-oxazolyl H).

Workup

  1. additionwas added dropwise at 0° C
  2. concentrationconcentrated
  3. additionThe residue was treated with 150 ml of water
  4. filtrationThe resulting mixture was filtered

Sources & evidence

ORD record
ord-6c845ff382d542a48824ea028c345515
Source dataset
uspto-grants-1995_11
Patent number
US05470862

Reaction notes

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