Methyl iodide → HCID 90029906, compound

HRID 1488071Notes

Reaction equation

HRID 1488071 reaction equation
[I:1][C:2]1[N:6]([CH2:7][O:8][CH2:9][CH2:10][Si:11]([CH3:14])([CH3:13])[CH3:12])[C:5]([C:15]2([OH:19])[CH2:18][O:17][CH2:16]2)=[N:4][C:3]=1[CH3:20].[H-].[Na+].[CH3:23]I>O1CCCC1>[I:1][C:2]1[N:6]([CH2:7][O:8][CH2:9][CH2:10][Si:11]([CH3:14])([CH3:13])[CH3:12])[C:5]([C:15]2([O:19][CH3:23])[CH2:18][O:17][CH2:16]2)=[N:4][C:3]=1[CH3:20]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 90029991HCID 90029991, compound2×

Product 1

HCID 90029906HCID 90029906, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into a 100-mL round-bottom flask, was placed a solution of 3-(5-iodo-4-methyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-2-yl)oxetan-3-ol (compound 192.3, 800 mg, 1.95 mmol) in tetrahydrofuran (30 mL). This was followed by the addition of sodium hydride (156.2 mg, 3.9 mmol, 60%) at 0° C. and stirred for 20 min at room temperature. To this was added CH3I (554.1 mg, 3.90 mmol) at 0° C. The resulting solution was stirred for 5 h at room temperature, then quenched with 30 mL of Na2S2O3 (sat.). The aqueous phase was extracted with 3×40 mL of ethyl acetate, the combined organic layers were washed with 3×40 mL of brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (1:2) eluent to furnish 700 mg (85%) of the title compound as colorless oil.

Workup

  1. customInto a 100-mL round-bottom flask, was placed
  2. stirringThe resulting solution was stirred for 5 h at room temperature
  3. customquenched with 30 mL of Na2S2O3 (sat.)
  4. extractionThe aqueous phase was extracted with 3×40 mL of ethyl acetate
  5. washthe combined organic layers were washed with 3×40 mL of brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (1:2) eluent

Sources & evidence

ORD record
ord-b68ae4f97f78429e8fac4dd0ef64b6b1
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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