Methyl iodide → HCID 23458318, compound

HRID 903950Notes

Reaction equation

HRID 903950 reaction equation
[OH:1][CH:2]([CH:5]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][CH3:14])[C:3]#[N:4].[CH3:21]I.[H-].[Na+]>CN(C=O)C.O>[CH3:21][O:1][CH:2]([CH:5]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][CH3:14])[C:3]#[N:4]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 15572607HCID 15572607, compound

Product 1

HCID 23458318HCID 23458318, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

b 2.69 g of 2-hydroxy-3-phenyl-3-(2-methoxy-phenoxy)-propionitrile dissolved in 25 ml of anhydrous DMF and 7.1 g of methyl iodide were stirred at 0° C. Addition was made, in portions, of 2.18 g of 55% NaH. After the addition, the whole was stirred at 0°-5° C. for 1 and a half hours. Under an atmosphere of nitrogen the whole was then decomposed cautiously with water, diluted with plentiful water, extracted with ethyl acetate and washed with water. The organic phase was dried over Na2SO4 and evaporated to dryness, in this way obtaining 1.95 g of 2-methoxy-3-phenyl-3-(2-methoxy-phenoxy)-propionitrile as an oil. Yield=69%. Analogously, all the 2-methoxy-propionitrile derivatives useful for the preparation of the 2-methoxy-propylamines listed in example 2 and obtained according to the reduction of Example 3, were prepared.

Workup

  1. additionAddition
  2. additionAfter the addition
  3. extractionextracted with ethyl acetate
  4. washwashed with water
  5. dry with materialThe organic phase was dried over Na2SO4
  6. customevaporated to dryness, in this way

Sources & evidence

ORD record
ord-c814aa9e8f4f406787d3c80ae2ffc61c
Source dataset
uspto-grants-1980_10
Patent number
US04229449

Reaction notes

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