Sodium hydride → 4-Bromo-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-imidazole

HRID 913054Notes

Reaction equation

[Br:1][C:2]1[NH:6][CH:5]=[N:4][CH:3]=1.[H-].[Na+].[CH3:9][Si:10]([CH2:13][CH2:14][O:15][CH2:16]Cl)([CH3:12])[CH3:11]>C1COCC1>[Br:1][C:2]1[N:6]=[CH:5][N:4]([CH2:16][O:15][CH2:14][CH2:13][Si:10]([CH3:12])([CH3:11])[CH3:9])[CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 5-bromo-1H-imidazole (1.0 eq.) in thy THF (0.4 M solution) was added NaH (60%, 1.2 eq.) portionwise at 0° C. The mixture was stirred for 2 hr at 0° C., then SEMCl (1.2 eq.) was added and the mixture was stirred for 12 hr at RT. The reaction was quenched by the addition of sat. aq. NH4Cl solution and the mixture extracted with EtOAc. The organic layer was washed with brine, dried (Na2SO4) and concentrated under reduced pressure. The crude was purified by column chromatography on silica gel eluting with 20-50% EtOAc/petroleum ether to obtain E1 as an oil. 1H NMR (300 MHz, CDCl3) δ: 7.45 (1H, s), 7.00 (1H, s), 5.21 (2H, s), 3.47 (2H, t, J=8.2 Hz), 0.89 (2H, t, J=8.2 Hz), 0.00 (9H, s). MS (ES) C9H17BrN2OSi requires: 276/278, found: 277/279 (M+H)+.

Workup

stirringthe mixture was stirred for 12 hr at RT
customThe reaction was quenched by the addition of sat. aq. NH4Cl solution
extractionthe mixture extracted with EtOAc
washThe organic layer was washed with brine
dry with materialdried (Na2SO4)
concentrationconcentrated under reduced pressure
customThe crude was purified by column chromatography on silica gel eluting with 20-50% EtOAc/petroleum ether

Sources & evidence

ORD record: ord-112807bad0fc4e06a479ad45dafe5d9c
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08026265B2

Reaction notes

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