Diethyl Malonate → ethyl 2-carbethoxy-3-(1-benzyl-1H-imidazol-2-yl)propanoate

HRID 2268278Notes

Reaction equation

[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[Na].Cl.[CH2:14]([N:21]1[CH:25]=[CH:24][N:23]=[C:22]1[CH2:26]Cl)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(O)C>[C:1]([CH:2]([CH2:26][C:22]1[N:21]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:25]=[CH:24][N:23]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4])([O:9][CH2:10][CH3:11])=[O:8]

Participants

Conditions

Temperature: 0 °C

Procedure

Diethyl malonate (52.45 g) in ethanol (50 ml) was added dropwise to a solution of sodium (11.3 g) in dry ethanol (300 ml) with stirring. The mixture was cooled to 0° C. and a solution of 1-benzyl-2-chloromethylimidazole hydrochloride (40.0 g, prepared as described in J.A.C.S. 1949, 383) in dry ethanol (250 ml) was added over 30 minutes with stirring. The mixture was stirred at ambient temperature for 2 hours and then the ethanol removed under reduced pressure. Ice cold 2M hydrochloric acid (400 ml) was added to the residue and the mixture was washed with ether. The aqueous layer was basified with solid sodium carbonate and then extracted with dichloromethane to give ethyl 2-carbethoxy-3-(1-benzyl-1H-imidazol-2-yl)propanoate as an oil.

Workup

stirringwith stirring
stirringThe mixture was stirred at ambient temperature for 2 hours
customthe ethanol removed under reduced pressure
additionIce cold 2M hydrochloric acid (400 ml) was added to the residue
washthe mixture was washed with ether
extractionextracted with dichloromethane

Sources & evidence

ORD record: ord-deb34f08870d41e5a43bf157f740e15d
Source dataset: uspto-grants-2001_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06326500B1

Reaction notes

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