Methyl iodide → 25310-30-9

HRID 885256Notes

Reaction equation

HRID 885256 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][C:10]#[N:11])[CH:6]=[CH:7][CH:8]=1.IC.[CH3:14][Si]([N-][Si](C)(C)C)(C)C.[Na+]>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]([CH3:14])[C:10]#[N:11])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 88310(3-Methoxyphenyl)acetonitrileHCID 2724254Sodium bis(trimethylsilyl)amide

Product 1

HCID 1361587025310-30-9

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To (3-methoxyphenyl)acetonitrile (1.0 g, 6.79 mmol) and iodomethane (0.42 mL, 6.79 mmol) in THF (10 mL) at 0° C. was added sodium bis(trimethylsilyl)amide (1M in THF; 6.8 mL, 6.8 mmol). The reaction was warmed to room temperature and stirred for 1 hour. The mixture was partitioned between H2O and EtOAc and acidified with 1N aqueous HCl, and then extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered, and concentrated to give the desired product.

Workup

  1. customThe mixture was partitioned between H2O and EtOAc
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0969d848989f4e08adb2ea521baa1961
Source dataset
uspto-grants-2012_08
Patent number
US08242145B2

Reaction notes

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