Formaldehyde → HCID 68487065, compound

HRID 1875118Notes

Reaction equation

HRID 1875118 reaction equation
[Li]CCCC.Br[C:7]1[N:8]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[C:9]([Cl:13])=[C:10]([Cl:12])[N:11]=1.[CH2:22]=[O:23]>C1COCC1>[Cl:12][C:10]1[N:11]=[C:7]([CH2:22][OH:23])[N:8]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[C:9]=1[Cl:13]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 586258532-Bromo-4,5-dichloro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazoleHCID 178418339Butyllithium

Product 1

HCID 68487065HCID 68487065, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

nBuLi (2.0 mL, 3.2 mmol, 1.6 M in hexane) was added dropwise to a solution of 2-bromo-4,5-dichloro-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole (1.1 g, 3.2 mmol) in THF (50 mL) at −78° C. under N2. The mixture was stirred for 30 min and paraformaldehyde (960 mg, 32 mmol) was then added. The mixture was allowed warm up to room temperature and stirred for 6 h and then quenched by aqueous NH4Cl. Extracted with EtOAc and the organic layer was dried over sodium sulfate and concentrated. The residue was purified by column chromatography (0-30% EtOAc in hexane) to give the title compound (614 mg, 65%) as a colorless oil. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 5.37 (2H, s) 4.70 (2H, d, J=1.2 Hz) 3.58 (2H, dd, J=8.9, 7.7 Hz) 0.89-0.96 (2H, m) 0.00 (9H, s). LCMS: m/z 297 (M+1).

Workup

  1. stirringstirred for 6 h
  2. customquenched by aqueous NH4Cl
  3. extractionExtracted with EtOAc
  4. dry with materialthe organic layer was dried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (0-30% EtOAc in hexane)

Sources & evidence

ORD record
ord-39aa322457254693bf9ab0a49f5d7a88
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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