Potassium Carbonate → 3,4-Dihydro-6-(2,2,2-trifluoroethoxy)-1(2H)-naphthalenone

HRID 63086

Reaktionsgleichung

Reaktionsgleichung von HRID 63086
[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.S(C1C=CC(C)=CC=1)(O[CH2:17][C:18]([F:21])([F:20])[F:19])(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[F:19][C:18]([F:21])([F:20])[CH2:17][O: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

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 67942Ethanol, 2,2,2-trifluoro-, 1-(4-methylbenzenesulfonate)HCID 46794946-Hydroxy-3,4-dihydro-1(2H)-naphthalenone

Produkt 1

HCID 618344413,4-Dihydro-6-(2,2,2-trifluoroethoxy)-1(2H)-naphthalenoneAusbeute 85,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 6-hydroxy-3,4-dihydro-1(2H)-naphthalenone (200 mg, 1.2 mmol) and 2,2,2-trifluoroethyl tosylate (345 mg, 1.4 mmol) in DMF (10 mL) was added potassium carbonate (339 mg, 2.5 mmol) at rt. The solution was heated at 100° C. overnight. The reaction was cooled, diluted with water (20 mL), and extracted with EtOAc (20 mL×3). Organics were dried (Na2SO4) and concentrated to give 250 mg (83%) of the title compound as a yellow solid. 1H NMR (300 MHz, CDCl3): δ 2.12-2.16 (2H, m), 2.64 (2H, t, J=6.3 Hz), 2.95 (2H, t, J=6.3 Hz), 4.34-4.46 (2H, m), 6.78 (1H, d, J=2.4 Hz), 6.87 (1H, dd, J=2.4, 8.7 Hz), 8.05 (1H, dd, J=8.7 Hz).

Aufarbeitung

  1. temperatureThe reaction was cooled
  2. extractionextracted with EtOAc (20 mL×3)
  3. dry with materialOrganics were dried (Na2SO4)
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-db0c1667d2304f96b8e73f61e2b6970b
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447045B2

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