Hydrochloric Acid → OXO-(2-OXO-TETRAHYDRO-FURAN-3-YL)-ACETIC ACID ETHYL ESTER

HRID 2268812Notes

Reaction equation

N[C@H](C=O)CCSC.[C:9]([O:16][CH2:17][CH3:18])(=[O:15])[C:10]([O:12]CC)=O.[C:19]1(=[O:24])[O:23][CH2:22][CH2:21][CH2:20]1.Cl>C(O)C>[O:24]=[C:19]1[CH:20]([C:10](=[O:12])[C:9]([O:16][CH2:17][CH3:18])=[O:15])[CH2:21][CH2:22][O:23]1

Participants

Conditions

Temperature: -12.5 °C

Procedure

Metal sodium in an amount of 25.80 g was added to 500 ml of dried ethanol and dissolved therein. Then, 148.21 g of diethyl oxalate were added, and the reaction system was chilled to −15 to −10° C. A solution of 88.79 g of γ-butyrolactone in 60 ml of ethanol was added dropwise to the mixture while maintaining this temperature, and after the resultant mixture was stirred for 2 hours, it was stirred at room temperature for 16 hours. The reaction mixture was poured into 1 liter of ice water, and the pH of the mixture was then adjusted to 4 to 5 with concentrated hydrochloric acid, and the mixture was extracted with chloroform. The chloroform layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The crude product thus obtained was distilled under reduced pressure to give a fraction of 150 to 160° C. (5-6 mmHg) as the intended product. Pale yellow liquid, 156.21 g (yield: 83.1%).

Workup

dissolutiondissolved
temperaturewhile maintaining this temperature
extractionthe mixture was extracted with chloroform
dry with materialThe chloroform layer was dried over anhydrous sodium sulfate
distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record: ord-63cde5920455422681d8c15b2c3b78ec
Source dataset: uspto-grants-2001_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06329382B1

Reaction notes

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