Water → HCID 86640397, compound

HRID 1806964Notes

Reaction equation

HRID 1806964 reaction equation
[OH:1][CH2:2][C:3]([CH3:8])([CH3:7])[CH2:4][C:5]#[N:6].[H-].[Na+].I[CH3:12].O>CN(C)C=O>[CH3:12][O:1][CH2:2][C:3]([CH3:8])([CH3:7])[CH2:4][C:5]#[N:6]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 14027412HCID 14027412, compound

Product 1

HCID 86640397HCID 86640397, compoundYield 95.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Step C To the solution of 4-hydroxy-3,3-dimethyl-butyronitrile (0.8 g, 7 mmol) in anhydrous dimethylformamide (5 mL) was added NaH (60%, 0.42 g, 11 mmol). The mixture was stirred at room temperature for 15 min, then iodomethane (0.88 mL, 14 mmol) was added. The mixture was stirred at room temperature for 1 h. Water was added. The mixture was extracted with ethyl acetate twice. The combined organic layers were washed with brine, dried over MgSO4, and concentrated to give 4-methoxy-3,3-dimethyl-butyronitrile as a yellow oil (0.85 g, 94%).

Workup

  1. stirringThe mixture was stirred at room temperature for 1 h
  2. extractionThe mixture was extracted with ethyl acetate twice
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a421c222660745a0a8160c88a05a836f
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

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