Methyl iodide → HCID 66914986, compound

HRID 880425Notes

Reaction equation

HRID 880425 reaction equation
[H-].[Na+].[CH3:3][O:4][CH2:5][N:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:8]=[C:7]1[CH2:17][OH:18].[CH3:19]I.[Cl-].[NH4+]>O1CCCC1>[CH3:3][O:4][CH2:5][N:6]1[CH:10]=[C:9]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:8]=[C:7]1[CH2:17][O:18][CH3:19]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 66914812HCID 66914812, compound

Product 1

HCID 66914986HCID 66914986, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (400 mg 1.83 mmol, 60%) was added to a solution of (1-methoxymethyl-4-phenyl-1H-pyrrol-2-yl)-methanol (420 mg, 2.08 mmol) in tetrahydrofuran (15 mL) at 0° C. and stirred for a further 15 min. Methyl iodide (517 mg, 3.66 mmol) was added and the reaction mixture stirred for 12 h. The mixture was poured into saturated aqueous ammonium chloride and extracted with ethyl acetate (2×50 mL). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo to afford 1,2-bis(methoxymethyl)-4-phenyl-pyrrole (300 mg, 72%) as a brown liquid.

Workup

  1. stirringthe reaction mixture stirred for 12 h
  2. extractionextracted with ethyl acetate (2×50 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1645e46a81a34a6799ac365513078bde
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

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