Ethyl 3-(2,4-dimethyl-imidazol-1-yl)-benzoate → 3-[3-(2,4-Dimethyl-imidazol-1-yl)-phenyl]-3-oxo-propionic acid tert.-butyl ester

HRID 1745534Notes

Reaction equation

HRID 1745534 reaction equation
[CH3:1][C:2]1[N:3]([C:8]2[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=2)[C:11]([O:13]CC)=O)[CH:4]=[C:5]([CH3:7])[N:6]=1.[C:19]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])(=[O:21])[CH3:20].[Li]>>[C:23]([O:22][C:19](=[O:21])[CH2:20][C:11]([C:10]1[CH:16]=[CH:17][CH:18]=[C:8]([N:3]2[CH:4]=[C:5]([CH3:7])[N:6]=[C:2]2[CH3:1])[CH:9]=1)=[O:13])([CH3:26])([CH3:25])[CH3:24]

Participants

3

Reactant 2

HCID 22224974Ethyl 3-(2,4-dimethyl-imidazol-1-yl)-benzoateHCID 86586795Lithium Tert-butyl Acetate

Product 1

HCID 695928063-[3-(2,4-Dimethyl-imidazol-1-yl)-phenyl]-3-oxo-propionic acid tert.-butyl ester

Procedure

Prepared from ethyl 3-(2,4-dimethyl-imidazol-1-yl)-benzoate [prepared by reaction of ethyl 3-aminobenzoate with ethyl acetimidate hydrochloride in EtOH at 0° C., direct treatment with 2-aminopropionaldehyde dimethyl acetal in EtOH at 23° C., follwed by addition of conc. H2SO4 and refluxing.] by treatment with lithium tert.-butyl acetate according to general procedure H (method b). Obtained as a yellow-brown oil (6.00 g).

Sources & evidence

ORD record
ord-5b7313e386a545e59e6ff95e40e7abbb
Source dataset
uspto-grants-2006_03
Patent number
US07018998B2

Reaction notes

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