Methyl iodide → HCID 18366007, compound

HRID 380739Notes

Reaction equation

HRID 380739 reaction equation
[OH:1][CH:2]1[CH2:6][O:5][CH2:4][CH:3]1[O:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=1[O:16][CH3:17])[C:11]#[N:12].[H-].[Na+].[CH3:20]I>CN(C)C=O>[CH3:17][O:16][C:15]1[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][C:8]=1[O:7][CH:3]1[CH:2]([O:1][CH3:20])[CH2:6][O:5][CH2:4]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 18366005HCID 18366005, compound

Product 1

HCID 18366007HCID 18366007, compoundYield 72.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
60 °C

Procedure

1.0 g (4.2 mmol) of 3-(4-hydroxytetrahydrofuran-3-yloxy)-4-methoxybenzonitrile (A15) in 5 ml of dimethylformamide is added dropwise under a nitrogen atmosphere to a solution of 140 mg (4.6 mmol) of 80% strength sodium hydride in 5 ml of dimethylformamide and the mixture is heated at 60° C. for 20 min. 315 μl (5.0 mmol) of methyl iodide, dissolved in 1 ml of dimethylformamide, are then added dropwise at RT. The mixture is stirred at RT for 2 h, concentrated, treated with 20 ml of water and acidified with 2 N hydrochloric acid. After extraction with 3×30 ml of ethyl acetate, the combined organic phases are dried over magnesium sulfate, concentrated and the crude product is recrystallized from 10 ml of isopropanol. 760 mg of the title compound of m.p. 98-100° C. are obtained.

Workup

  1. additionare then added dropwise at RT
  2. concentrationconcentrated
  3. additiontreated with 20 ml of water
  4. extractionAfter extraction with 3×30 ml of ethyl acetate
  5. dry with materialthe combined organic phases are dried over magnesium sulfate
  6. concentrationconcentrated
  7. customthe crude product is recrystallized from 10 ml of isopropanol

Sources & evidence

ORD record
ord-1882e4911e064a1cbc082c5aa7611f9d
Source dataset
uspto-grants-2001_10
Patent number
US06303789B1

Reaction notes

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