Methyl iodide → HCID 68721300, compound

HRID 1875222Notes

Reaction equation

HRID 1875222 reaction equation
[H-].[Na+].[Br:3][C:4]1[N:5]=[C:6]([CH:18]([OH:20])C)[N:7]([CH2:10][O:11][CH2:12][CH2:13][Si:14]([CH3:17])([CH3:16])[CH3:15])[C:8]=1[Br:9].I[CH3:22]>C1COCC1>[Br:3][C:4]1[N:5]=[C:6]([CH2:18][O:20][CH3:22])[N:7]([CH2:10][O:11][CH2:12][CH2:13][Si:14]([CH3:17])([CH3:16])[CH3:15])[C:8]=1[Br:9]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 68724180HCID 68724180, compound

Product 1

HCID 68721300HCID 68721300, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

NaH (0.016 g of a 60% dispersion in mineral oil, 0.41 mmol) was added to a 0° C. solution of [4,5-dibromo-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazol-2-yl]ethanol (0.15 g, 0.39 mmol) in THF (2 mL). The solution was stirred at RT for 30 mins, recooled to 0° C. and iodomethane was added (0.052 mL, 0.78 mmol). After 2 h at RT, the reaction mixture was quenched by addition of sat'd NaHCO3 and extracted with CH2Cl2. The organic phase was dried (Na2SO4), filtered, and purified by silica gel chromatography (0-30% EtOAc/hex) to afford the title compound (0.084 g, 54%) as clear oil. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 5.39 (s, 2H), 4.55 (s, 2H), 3.57 (t, J=8.19 Hz, 2H), 3.35 (s, 3H), 0.91 (t, J=8.15 Hz, 2H), −0.01 (s, 9H).

Workup

  1. customrecooled to 0° C.
  2. waitAfter 2 h at RT
  3. customthe reaction mixture was quenched by addition of sat'd NaHCO3
  4. extractionextracted with CH2Cl2
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. filtrationfiltered
  7. custompurified by silica gel chromatography (0-30% EtOAc/hex)

Sources & evidence

ORD record
ord-e6a6699e18734414a635c4cedbb90314
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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