Methyl iodide → 2-(5-Chloro-2-isopropyl-4-methoxy-phenoxy)-3-methoxy-acrylonitrile

HRID 2266079Notes

Reaction equation

HRID 2266079 reaction equation
[Cl:1][C:2]1[C:3]([O:15][CH3:16])=[CH:4][C:5]([CH:12]([CH3:14])[CH3:13])=[C:6]([CH:11]=1)[O:7][CH2:8][C:9]#[N:10].[CH:17]([O:19][CH2:20]C)=O.[H-].[Na+].IC>COCCOC>[Cl:1][C:2]1[C:3]([O:15][CH3:16])=[CH:4][C:5]([CH:12]([CH3:14])[CH3:13])=[C:6]([CH:11]=1)[O:7][C:8](=[CH:17][O:19][CH3:20])[C:9]#[N:10]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8025Ethyl formateHCID 24758Sodium hydride2×HCID 59598662(5-Chloro-2-isopropyl-4-methoxy-phenoxy)-acetonitrile

Product 1

HCID 670534222-(5-Chloro-2-isopropyl-4-methoxy-phenoxy)-3-methoxy-acrylonitrileYield 84%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of (5-chloro-2-isopropyl-4-methoxy-phenoxy)-acetonitrile (1.44 g, 6.0 mmol) and ethyl formate (2.2 g, 29.2 mmol) in 7 mL 1,2-dimethoxy ethane at 5° C. was added 95% NaH (0.15 g, 6.0 mmol) in one portion. The mixture was warmed to room temperature. After 1 hour 95% NaH (0.15 g, 6.0 mmol) was added in one portion. After 1 hour 10 mL iodomethane was added and the mixture was allowed to stir for 16 hour. The mixture was concentrated in vacuo, 1N HCl was added and the mixture was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. Purification via flash chromatography (85:15 hexane/ethyl acetate) afforded 2-(5-chloro-2-isopropyl-4-methoxy-phenoxy)-3-methoxy-acrylonitrile (1.41 g, 84%) as a white solid.

Workup

  1. concentrationThe mixture was concentrated in vacuo, 1N HCl
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification via flash chromatography (85:15 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-b580391eefdd4bfdb07c5a811c5152f2
Source dataset
uspto-grants-2010_12
Patent number
US07858632B2

Reaction notes

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