Methyl iodide → HCID 68663038, compound

HRID 452722Notes

Reaction equation

HRID 452722 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][C:10]3[O:14][CH:13]=[C:12]([C:15]4[CH:20]=[CH:19][C:18]([CH2:21][OH:22])=[CH:17][CH:16]=4)[C:11]=3[CH:23]=2)=[N:4][N:3]=1.O1CCC[CH2:25]1.[H-].[Na+].IC>C(OCC)(=O)C.CN(C)C=O>[CH3:25][O:22][CH2:21][C:18]1[CH:19]=[CH:20][C:15]([C:12]2[C:11]3[CH:23]=[C:7]([C:5]4[O:6][C:2]([CH3:1])=[N:3][N:4]=4)[CH:8]=[CH:9][C:10]=3[O:14][CH:13]=2)=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 68664421HCID 68664421, compound

Product 1

HCID 68663038HCID 68663038, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of [4-[5-(5-methyl-1,3,4-oxadiazol-2-yl)-1-benzofuran-3-yl]phenyl]methanol (193 mg, 0.630 mmol), tetrahydrofuran (3 mL) and N,N-dimethylformamide (3 mL) was added sodium hydride (60% in oil, 37.8 mg, 0.945 mmol) at room temperature, and the resulting mixture was stirred for 10 min. Iodomethane (0.0588 mL, 0.945 mmol) was added to the reaction mixture, and the mixture was further stirred at room temperature for 1 hr. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (hexane/tetrahydrofuran=2/1), and crystallized from hexane/tetrahydrofuran to give the title compound (146 mg, yield 73%) as colorless crystals.

Workup

  1. stirringthe mixture was further stirred at room temperature for 1 hr
  2. washwashed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by basic silica gel column chromatography (hexane/tetrahydrofuran=2/1)
  6. customcrystallized from hexane/tetrahydrofuran

Sources & evidence

ORD record
ord-cdaf04f9cf064b0f9b7b1ebf0dbdf338
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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