Ethanol → HCID 67120707, compound

HRID 2365583Notes

Reaction equation

HRID 2365583 reaction equation
[OH-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][C:20]#[N:21])=[CH:15][CH:14]=2)=[CH:6][CH:5]=1.CCO>>[F:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][O:12][C:13]2[CH:14]=[CH:15][C:16]([CH2:19][CH2:20][NH2:21])=[CH:17][CH:18]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 67086776HCID 67086776, compound

Product 1

HCID 67120707HCID 67120707, compound

Procedure

2 N NaOH solution (45.2 ml, 90.3 mmol) is added to a solution of {4-[2-(4-Fluoro-phenyl)-ethoxy]-phenyl}-acetonitrile (3.29 g, 12.9 mmol) in EtOH (45.2 mol) followed by Al—Ni Alloy (2.5 g) and the resulting reaction mixture is stirred for 1 hour at room temperature. The reaction mixture is filtered and the EtOH removed in vacuo. The product is extracted into DCM (2×80 ml), dried (MgSO4) and the solvent removed in vacuo to yield the title compound as a yellow oil.

Workup

  1. customthe resulting reaction mixture
  2. filtrationThe reaction mixture is filtered
  3. customthe EtOH removed in vacuo
  4. extractionThe product is extracted into DCM (2×80 ml)
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-417d005cbc11486a9c3c3193a4ac1cc4
Source dataset
uspto-grants-2014_04
Patent number
US08697687B2

Reaction notes

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