Methyl iodide → HCID 12603267, compound

HRID 224658Notes

Reaction equation

HRID 224658 reaction equation
[H-].[Na+].[C:3]([C:11]1[CH:15]=[C:14]([CH3:16])[N:13]([CH:17]([CH3:20])[CH2:18][OH:19])[C:12]=1[CH3:21])(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:22]I>C(COC)OC>[CH3:22][O:19][CH2:18][CH:17]([N:13]1[C:14]([CH3:16])=[CH:15][C:11]([C:3](=[O:10])[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)=[C:12]1[CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 194460[1-(1-Hydroxypropan-2-yl)-2,5-dimethyl-1H-pyrrol-3-yl](phenyl)methanone

Product 1

HCID 12603267HCID 12603267, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Sodium hydride (50% content, 115 mg, 2.3 mmoles) was washed with 20 ml of petroleum ether twice, and 15 ml of dimethoxyethane was added. To the mixture was added 300 mg (1.17 mmoles) of 2-(3-benzoyl-2,5-dimethylpyrrol-1-yl)-2-methylethanol, and the mixture was stirred at room temperature for 2 hours. Then, 5 ml of methyl iodide was added, and the mixture was further stirred at room temperature for 5 hours. After the reaction, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated to afford 270 mg of a crude product. The product was chromatographed on a column of silica gel using cyclohexane/ethyl acetate (4/1) as an eluent to afford compound (206) (220 mg, 0.81 mmole, 69.4%).

Workup

  1. stirringthe mixture was further stirred at room temperature for 5 hours
  2. customAfter the reaction
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customto afford 270 mg of a crude product
  8. customThe product was chromatographed on a column of silica gel

Sources & evidence

ORD record
ord-d5f2f3b532cb40f2b8957a54cd97d33a
Source dataset
uspto-grants-1980_11
Patent number
US04233309

Reaction notes

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