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

HRID 422216Notes

Reaction equation

HRID 422216 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

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 411 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).

Workup

  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

Sources & evidence

ORD record
ord-0b8ace4baf1e4d91a3d3c83c5d28a9e8
Source dataset
uspto-grants-2012_01
Patent number
US08101638B2

Reaction notes

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