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Water → 2-[5-Methoxy-2-(4-methoxy-phenyl)-benzofuran-7-yl]-propionitrile

HRID 1794479
Notes
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Reaction equation

HRID 1794479 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:20][C:21]#[N:22])[C:6]2[O:10][C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)=[CH:8][C:7]=2[CH:19]=1.[OH-].[K+].[CH3:25]I.O>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:20]([CH3:25])[C:21]#[N:22])[C:6]2[O:10][C:9]([C:11]3[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=3)=[CH:8][C:7]=2[CH:19]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 10308348HCID 10308348, compound

Product 1

HCID 222215942-[5-Methoxy-2-(4-methoxy-phenyl)-benzofuran-7-yl]-propionitrileYield 42%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

To a solution of acetonitrile 18 (0.200 g, 0.682 mmole) in 10 mL dimethylformamide was added pulverized potassium hydroxide (0.046 g, 0.818 mmole) and methyl iodide (0.161 g, 0.818 mmole). After stirring at rt for 2 hours, the orange reaction mixture was poured into water and extracted with ethyl acetate. The combined organic phases were washed with saturated sodium bicarbonate, water, brine, and dried with magnesium sulfate. The organic phases were concentrated and the residue was loaded on to silica gel and chromatographed with silica gel (hexanes:ethyl acetate, 95:5) to afford 0.087 g (42%) of propionitrile 19 as a white solid. Used as is for conversion to 21, infra.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic phases were washed with saturated sodium bicarbonate, water, brine
  3. dry with materialdried with magnesium sulfate
  4. concentrationThe organic phases were concentrated
  5. customchromatographed with silica gel (hexanes:ethyl acetate, 95:5)

Sources & evidence

ORD record
ord-6a56c5175e6e4f47bad3bf755d0dd984
Source dataset
uspto-grants-2006_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07022733B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes