Diethyl Oxalate → 2,4-Dioxo-4-thiazol-2-yl-butyric acid ethyl ester

HRID 129835

Reaction equation

HRID 129835 reaction equation
[C:1]([O:8][CH2:9][CH3:10])(=[O:7])[C:2]([O:4]CC)=O.[C:11]([C:14]1[S:15][CH:16]=[CH:17][N:18]=1)(=[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[S:15][CH:16]=[CH:17][N:18]=1)[CH3:10]

Participants

4

Reactant 2

HCID 7268Diethyl OxalateHCID 5201082-Acetylthiazole

Product 1

HCID 537614132,4-Dioxo-4-thiazol-2-yl-butyric acid ethyl esterYield 72.2%

Reagents, catalysts & solvents 1

HCID 2723922Sodium ethoxideSolvent

Procedure

To a sodium ethoxide solution (prepared from 150 ml of ethanol and 4.2 g of sodium) at 0° C., a mixture of diethyl oxalate (22.98 g) and acetylthiazole (20.07 g) was added dropwise. The resulting mixture was stirred at room temperature for 2 hours and concentrated. The residue was treated with 100 ml of water and neutralized with 6N HCl. Filtration afforded 25.8 g of 2,4-diketo-4-(thiazol-2-yl)butyric acid ethyl ester as brown solids. NMR: 1.46 (t, 3H), 4.49 (q, 2H), 7.27 (s, 1H), 7.65, 8.04 (2d, 2H, thiazolyl H's).

Workup

  1. additionwas added dropwise
  2. concentrationconcentrated
  3. additionThe residue was treated with 100 ml of water and neutralized with 6N HCl
  4. filtrationFiltration

Sources & evidence

ORD record
ord-07e4f8c57880493e91f3b448105bb0cd
Source dataset
uspto-grants-1995_11
Patent number
US05470862

Linked notes

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