Potassium Carbonate → 4-(5-Oxo-5,6,7,8-tetrahydro-naphthalen-2-yloxy)-benzonitrile

HRID 422218Notes

Reaction equation

HRID 422218 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]2.F[C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=1.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.CC(N(C)C)=O>[O:12]=[C:8]1[CH2:7][CH2:6][CH2:5][C:4]2[CH:3]=[C:2]([O:1][C:14]3[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=3)[CH:11]=[CH:10][C:9]1=2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 145174-FluorobenzonitrileHCID 46794946-Hydroxy-3,4-dihydro-1(2H)-naphthalenone

Product 1

HCID 597506514-(5-Oxo-5,6,7,8-tetrahydro-naphthalen-2-yloxy)-benzonitrileYield 82%

Reagents, catalysts & solvents 1

HCID 66603805toluene N,N-dimethylacetamideSolvent

Procedure

Combine 6-Hydroxytetralone (4.42 g, 27.24 mmol), 4-Fluorobenzonitrile (3.0 g, 24.76 mmol), K2CO3 (5.1 g, 37.14 mmol) and toluene/DMA (30 ml/90 ml), then reflux under nitrogen using a Dean Stark Trap. After 4 hours, cool the reaction to room temperature and add to a separatory funnel. Add Ethyl acetate and wash the organic layer several times with water, then a brine solution, and dry the organic layer over Na2SO4. Flash chromatograph using 4/1 hexanes/ethyl acetate eluant to afford 5.34 g, 20.3 mmol (82% yield) of the title compound: 1H NMR (500 MHz, CDCl3); 2.1-2.2 (2H, m), 2.6-2.7 (2H, m), 2.9-3.0 (2H, m), 6.85 (1H, s), 6.9-7.0 (1H, m), 7.05-7.15 (2H, m), 7.6-7.7 (2H, m), 8.05-8.10 (1H, m); MS m/z 264 (M+1).

Workup

  1. temperaturecool
  2. customthe reaction to room temperature
  3. additionadd to a separatory funnel
  4. washAdd Ethyl acetate and wash the organic layer several times with water
  5. dry with materiala brine solution, and dry the organic layer over Na2SO4

Sources & evidence

ORD record
ord-9f7f316e6b5b481e8b57eedab102f133
Source dataset
uspto-grants-2012_01
Patent number
US08101638B2

Reaction notes

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