2-Vinylpyridine → Propanedioic acid, 2-[2-(2-pyridinyl)ethyl]-, 1,3-diethyl ester
Reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[O-]CC.[Na+].[CH:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)=[CH2:17]>>[N:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[CH2:16][CH2:17][CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:1]([O:9][CH2:10][CH3:11])=[O:8]Participants
Procedure
Diethyl β-(2-pyridyl)-ethylmalonate was prepared in the manner described by V. Boekelheide and S. Rothchild, JACS, 71, 879 (1949). Briefly, diethyl malonate (375 g, 2.35 moles) was added to a solution of sodium ethoxide (23 g of sodium in 225 mL of absolute alcohol). To the boiling mixture, freshly distilled 2-vinylpyridine (106 g, 1.0 mole) in 175 mL of absolute alcohol was added slowly. After the mixture had boiled under reflux for two hours, the alcohol was removed by distillation and the residue was acidified with dilute hydrochloric acid. The unreacted malonic ester was extracted with ether, the aqueous phase was made basic with dilute sodium hydroxide, and the basic organic layer was extracted with ether. After the ethereal solution had been dried over Drierite, the ether and recovered 2-vinylpyridine (boiling point 58° C. at 16 mm) were removed in vacuo.
Workup
- temperatureunder reflux for two hours
- customthe alcohol was removed by distillation
- extractionThe unreacted malonic ester was extracted with ether
- extractionthe basic organic layer was extracted with ether
- dry with materialAfter the ethereal solution had been dried over Drierite
- customthe ether and recovered 2-vinylpyridine (boiling point 58° C. at 16 mm)
- customwere removed in vacuo
Sources & evidence
- ORD record
- ord-f3f5125fa1b64123bcd2dbd73e060b83
- Source dataset
- uspto-grants-1995_11
- Patent number
- US05464830
Reaction notes
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