Formaldehyde → HCID 68722904, compound

HRID 1875221Notes

Reaction equation

HRID 1875221 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]([Br:13])=[C:10]([Br:12])[N:11]=1.[CH2:22]=[O:23]>C1COCC1>[Br: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[Br:13]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 109062032,4,5-tribromo-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-ImidazoleHCID 178418339Butyllithium

Product 1

HCID 68722904HCID 68722904, compoundYield 302%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

n-BuLi (3.16 mL of a 1.6 M solution in hexanes, 4.96 mmol) was added dropwise to a −78° C. solution of 2,4,5-tribromo-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole (2.16 g, 4.96 mmol) in THF (50 mL). After 30 min, paraformaldehyde (0.74 g, 24.82 mmol) was added. The reaction mixture was warmed to RT, stirred overnight, quenched by addition of sat'd NH4Cl and extracted with EtOAc. The organic phase was dried (Na2SO4), filtered, and purified by silica gel chromatography (5-60% EtOAc/hex) to afford the title compound (0.57 g, 302%) as a clear oil. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 5.44 (d, J=0.46 Hz, 2H), 4.74-4.88 (m, 2H), 3.49-3.69 (m, 2H), 0.88-1.02 (m, 2H), −0.13-0.22 (m, 9H).

Workup

  1. customquenched by addition of sat'd NH4Cl
  2. extractionextracted with EtOAc
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. filtrationfiltered
  5. custompurified by silica gel chromatography (5-60% EtOAc/hex)

Sources & evidence

ORD record
ord-4fe9b52064df4dd88d4372375d9dccc9
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

Loading…