Potassium Carbonate → 4-(1-Oxo-indan-5-yloxy)-benzonitrile

HRID 747966

反応式

HRID 747966 の反応式
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2.F[C:13]1[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+].C1(C)C=CC=CC=1.CC(N(C)C)=O>C(OCC)(=O)C>[O:11]=[C:7]1[C:8]2[C:4](=[CH:3][C:2]([O:1][C:13]3[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=3)=[CH:10][CH:9]=2)[CH2:5][CH2:6]1

参加物

6

反応物 4

HCID 11430Potassium CarbonateHCID 145174-FluorobenzonitrileHCID 2331475-Hydroxy-1-indanoneHCID 66603805toluene N,N-dimethylacetamide

生成物 1

HCID 597506434-(1-Oxo-indan-5-yloxy)-benzonitrile収率 51.3%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

Combine 5-Hydroxyindanone (2.0 g, 13.50 mmol), 4-Fluorobenzonitrile (1.55 g, 12.80 mmol), K2CO3 (2.65 g, 19.20 mmol) and toluene/DMA (20 ml/40 ml), reflux under Nitrogen using a Dean-Stark Trap. After 4.0 hours, cool the reaction to room temperature and add Ethyl Acetate. Wash several times with 10% LiCl and Brine solution, then dry the organic layer over Na2SO4 follow by concentration. Flash chromatograph using 4/1 then 1/1 hexanes/ethyl acetate eluant to afford 1.64 g, 6.57 mmol (49% yield) of the title compound: 1H NMR (500 MHz, CDCl3); 2.7-2.8 (2H, m), 3.1-3.2 (2H, m), 7.0-7.1 (2H, m), 7.1-7.2 (2H, m), 7.6-7.7 (2H, m), 7.7-7.8 (1H, m); MS m/z 250 (M+1).

後処理

  1. temperaturecool
  2. customthe reaction to room temperature
  3. washWash several times with 10% LiCl and Brine solution
  4. dry with materialdry the organic layer over Na2SO4
  5. concentrationfollow by concentration

出典と根拠

ORDレコード
ord-b6f0d1d89b4a4e5d83b20bef39093f66
出典データセット
uspto-grants-2008_07
特許番号
US07399774B2

関連ノート

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