Reaction equation
[C:1]([O:8][CH2:9][CH3:10])(=[O:7])[C:2]([O:4]CC)=O.CC[O-].[Na+].[Na].[C:16]([O:23][CH2:24][CH3:25])(=[O:22])[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]>O.C(O)C.CCOCC>[CH2:18]([CH:17]([C:2](=[O:4])[C:1]([O:8][CH2:9][CH3:10])=[O:7])[C:16]([O:23][CH2:24][CH3:25])=[O:22])[CH2:19][CH2:20][CH3:21]Participants
Procedure
100 ml of ether, then 13.55 ml of diethyl oxalate were added to a solution of sodium ethylate prepared by stirring 2.3 g of sodium and 150 ml of ethanol at 40° C. for one hour. The mixture was refluxed for 15 minutes, cooled down slightly and 50 ml of ethyl caproate were added. The mixture was stirred at reflux for 3 hours and at 30° C. to 35° C. for 16 hours. 50 ml of water were added and the aqueous phase was separated by decanting, washed twice with ether and acidified with 2N hydrochloric acid. Extraction was carried out 3 times with ether and the combined organic phases were washed with water, then with a saturated solution of sodium chloride, dried and evaporated to dryness to obtain 9.5 g of the desired product which was used as is for the following step.
Workup
- customprepared
- temperatureThe mixture was refluxed for 15 minutes
- temperaturecooled down slightly
- temperatureat reflux for 3 hours and at 30° C. to 35° C. for 16 hours
- customthe aqueous phase was separated
- customby decanting
- washwashed twice with ether
- extractionExtraction
- washthe combined organic phases were washed with water
- dry with materialwith a saturated solution of sodium chloride, dried
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-88d0b947f0114e4dae17c9002676060a
- Source dataset
- uspto-grants-1998_10
- Patent number
- US05817674
Linked notes
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