Tetrahydrofuran → HCID 68721172, compound

HRID 1875224Notes

Reaction equation

HRID 1875224 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.C1C[O:25][CH2:24][CH2:23]1>>[Br:12][C:10]1[N:11]=[C:7]([CH2:23][CH2:24][OH:25])[N:8]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[C:9]=1[Br:13]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 109062032,4,5-tribromo-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-ImidazoleHCID 178418339Butyllithium

Product 1

HCID 68721172HCID 68721172, compoundYield 31%

Procedure

n-BuLi (4.30 mL of a 1.6 M solution in hexanes, 6.80 mmol) was added dropwise to a −78° C. solution of 2,4,5-tribromo-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole (2.96 g, 6.80 mmol) in THF (55 mL). After 25 min, oxirane gas was bubbled through the solution for 25 mins. The reaction mixture was allowed to warm slowly to RT, stirred overnight, quenched by addition of sat'd NH4Cl and extracted with CH2Cl2. The organic phase was dried (Na2SO4), filtered, and purified by silica gel chromatography (5-50% EtOAc/hex) to afford the title compound (0.83 g, 31%) as a yellow oil. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 5.36 (s, 2H), 3.82 (t, J=6.09 Hz, 2H), 3.55 (dd, J=8.94, 7.65 Hz, 2H), 3.10 (br. s., 1H), 2.90 (t, J=6.09 Hz, 2H), 0.85-0.98 (m, 2H), −0.02 (s, 9H).

Workup

  1. customoxirane gas was bubbled through the solution for 25 mins
  2. customquenched by addition of sat'd NH4Cl
  3. extractionextracted with CH2Cl2
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. filtrationfiltered
  6. custompurified by silica gel chromatography (5-50% EtOAc/hex)

Sources & evidence

ORD record
ord-e856ce4a704f4e679c66fc5c27031b39
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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