Dimethylformamide → methyl 2-formyl-1-((2-(trimethylsilyl)-ethoxy)-methyl)-1H-imidazole-4-carboxylate

HRID 646904Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7](Br)[N:8]([CH2:10][O:11][CH2:12][CH2:13][Si:14]([CH3:17])([CH3:16])[CH3:15])[CH:9]=1)=[O:4].C([Mg]Cl)(C)C.CN([CH:27]=[O:28])C>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([CH:27]=[O:28])[N:8]([CH2:10][O:11][CH2:12][CH2:13][Si:14]([CH3:17])([CH3:16])[CH3:15])[CH:9]=1)=[O:4]

Participants

Conditions

Temperature: -40 °C

Procedure

To a solution of 2-bromo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-4-carboxylic acid methyl ester (0.25 g, 0.74 mmol) (as prepared in the previous step) in THF (3 mL) at −40° C. was added dropwise a solution of 2M i-PrMgCl in THF (0.37 mL, 0.74 mmol). The reaction was allowed to stir for 10 min at −40° C. and then cooled to −78° C. and DMF (0.3 mL) was added. The reaction was allowed to attain RT and stirred for 1 h. The reaction was quenched with saturated NH4Cl, diluted with EtOAc (10 mL) and washed with brine (2×10 mL) and the organic layer was concentrated. The title compound was eluted from a 10-g SPE cartridge (silica) with 50% EtOAc/hexane to give 0.11 g (53%) of a colorless oil. Mass spectrum (ESI, m/z): Calcd. for C12H20N2O4Si, 285.1 (M+H), found 284.7.

Workup

temperaturecooled to −78° C.
customto attain RT
stirringstirred for 1 h
customThe reaction was quenched with saturated NH4Cl
additiondiluted with EtOAc (10 mL)
washwashed with brine (2×10 mL)
concentrationthe organic layer was concentrated
washThe title compound was eluted from a 10-g SPE cartridge (silica) with 50% EtOAc/hexane

Sources & evidence

ORD record: ord-e87f528cadca4fda991251dfd9b8a143
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07705042B2

Reaction notes

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