Acetonitrile → HCID 53640530、化合物

HRID 2253449ノート

反応式

HRID 2253449 の反応式
[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

参加物

5

反応物 3

HCID 6342AcetonitrileHCID 14797Potassium HydroxideHCID 11723053HCID 11723053、化合物

生成物 1

HCID 53640530HCID 53640530、化合物収率 57%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-e13745079bc640f5999ac33b1e77fffc
出典データセット
uspto-grants-2008_01
特許番号
US07323587B2

反応ノート

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