Acetonitrile → HCID 53640530, compound

HRID 2253449Notes

Reaction equation

HRID 2253449 reaction equation
[OH-].[K+].[C:3]1(/[C:9](/[C:19]2[CH:24]=[CH:23][C:22]([CH:25]=O)=[CH:21][CH:20]=2)=[C:10](/[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)\[CH2:11][CH3:12])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:27][C:28]#[N:29]>O>[C:3]1([C:9]([C:19]2[CH:24]=[CH:23][C:22]([CH:25]=[CH:27][C:28]#[N:29])=[CH:21][CH:20]=2)=[C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:11][CH3:12])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 14797Potassium HydroxideHCID 11723053HCID 11723053, compound

Product 1

HCID 53640530HCID 53640530, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of potassium hydroxide (85%, 260 mg, 3.9 mmol) in CH3CN (25 mL) was heated to reflux and (Z)-1,2-Diphenyl-1-(4-formylphenyl)-1-butene (4a) (Willson J. Med. Chem. 1994, 37, 1550-1552) (1.0 g, 3.18 mmol) was added in portions. After refluxing 5 min the mixture was diluted with water and extracted with EtOAc. The combined organic layers were washed with water, brine and dried (MgSO4). The solvent was removed under reduced pressure and the residue chromatographed (silica gel, 15% EtOAc/hexanes) to give the nitrile (4b) as a white solid (616 mg, 57%): 1H NMR (CDCl3) δ 7.39-7.07 (m, 13H), 6.91 (d, J=8.4 Hz, 2H), 5.69 (d, J=16.9 Hz, 1H), 2.48 (q, J=7.3 Hz, 2H), 0.94 (t, J=7.3 Hz, 3H); HRMS calcd. for C25H21N (M+H+) 335.1674; found 335.1679.

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. temperatureAfter refluxing 5 min the mixture
  4. extractionextracted with EtOAc
  5. washThe combined organic layers were washed with water, brine
  6. dry with materialdried (MgSO4)
  7. customThe solvent was removed under reduced pressure
  8. customthe residue chromatographed (silica gel, 15% EtOAc/hexanes)

Sources & evidence

ORD record
ord-e13745079bc640f5999ac33b1e77fffc
Source dataset
uspto-grants-2008_01
Patent number
US07323587B2

Reaction notes

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