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ChemicalBook CAS DataBase List 4-CYCLOPROPYL-2,4-DIOXO-BUTYRIC ACID METHYL ESTER
167408-67-5

4-CYCLOPROPYL-2,4-DIOXO-BUTYRIC ACID METHYL ESTER synthesis

2synthesis methods
-

Yield:167408-67-5 55%

Reaction Conditions:

Stage #1: Dimethyl oxalate;1-cyclopropyl-ethanonewith methanol;sodium at 0 - 20;Reflux;
Stage #2: with sulfuric acid in diethyl ether;water; pH=2;

Steps:



Synthesis of compound 1 Na (14.67g, 0.64mol) was dissolved in dry MeOH (0.8L) and a solution of cyclo- propylmethylketone (50g, 0.59mol) and dimethyloxalate (70.2g, 0.59mol) in dry MeOH (0.2L) was added dropwise at 0°C. The reaction mixture was stirred at r.t. 24h and reflux overnight. Water (0.5L) was added and the methanol was removed under reduced pressure. The aqueous solution was washed with Et21H-NMR (CDCI3): δ= 14.61 (br, 1 H), 6.84 (s, 1 H), 3.90 (s, 3H), 1 .95-1 .82 (m, 1 H), 1.26- 1 .20 (m, 2H), 1 .10-1 .00 (m, 2H).

References:

WO2012/10633,2012,A1 Location in patent:Page/Page column 53