Dimethylformamide → 4-Chloro-2-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carbaldehyde

HRID 1875120Notes

Reaction equation

HRID 1875120 reaction equation
[Li]CCCC.[Cl:6][C:7]1[N:8]=[C:9]([CH2:21][O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])[N:10]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[C:11]=1Cl.CN([CH:33]=[O:34])C>C1COCC1>[Cl:6][C:7]1[N:8]=[C:9]([CH2:21][O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])[N:10]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[C:11]=1[CH:33]=[O:34]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 684838634,5-Dichloro-2-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazoleHCID 178418339Butyllithium

Product 1

HCID 715339744-Chloro-2-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carbaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

nBuLi (1.3 mL, 2.05 mmol, 1.57 M in hexane) was added dropwise to a solution of 4,5-dichloro-2-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole (842 mg, 2.05 mmol) in THF (30 mL) at −78° C. under N2. The mixture was stirred for 30 min and DMF (1.0 mL) was then added dropwise. The mixture was stirred for 20 min and then allowed warm up to room temperature and stirred for 20 min. Quenched by aqueous NH4Cl and extracted with EtOAc and the organic layer was dried over sodium sulfate and concentrated.

Workup

  1. stirringThe mixture was stirred for 20 min
  2. stirringstirred for 20 min
  3. customQuenched by aqueous NH4Cl
  4. extractionextracted with EtOAc
  5. dry with materialthe organic layer was dried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-429c126995b047d3b45ec5a608c1d3c5
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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