Dimethylformamide → 5-tert-Butyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carbaldehyde

HRID 7108

Reaction equation

[C:1]([C:5]1[N:9]([CH2:10][O:11][CH2:12][CH2:13][Si:14]([CH3:17])([CH3:16])[CH3:15])[CH:8]=[N:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Li]CCCC.CN([CH:26]=[O:27])C>>[C:1]([C:5]1[N:9]([CH2:10][O:11][CH2:12][CH2:13][Si:14]([CH3:17])([CH3:16])[CH3:15])[C:8]([CH:26]=[O:27])=[N:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Reactant 3

HCID 6228Dimethylformamide

HCID 220185695-tert-butyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole

HCID 178418339Butyllithium

Product 1

HCID 220186865-tert-Butyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carbaldehydeYield 99%

Procedure

Reaction 5-tert-butyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole (276 mg, 1.09 mmol), 2.5 M n-BuLi (567 uL, 1.42 mmol), and DMF (253 uL, 3.27 mmol) for 2 h at −40° C. gave the title compound (304 mg, 99%) as a yellow solid. 1H NMR (300 MHz, CDCl3) δ 0.00 (s, 9H), 0.91 (t, 2H, J=9.0 Hz), 1.33 (s, 9H), 3.57 (t, 2H, J=7.5 Hz), 5.72 (s, 2H), 7.10 (s, 1H), 9.80 (s, 1H).

Sources & evidence

ORD record: ord-d74faec5e83541cbbd0bd727ffa8fc30
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07084155B2

Linked notes

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