Water → 6-fluoro-3,4-dihydro-2-phenyl-1(2H)-naphthalenone

HRID 1646989Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1646989
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[C:7]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(C(OC)=O)[CH2:6][CH2:5]2.[Cl-].[Li+].O>CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH:7]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:6][CH2:5]2

Komponenten

5

Edukt 3

HCID 962WaterHCID 433294Lithium ChlorideHCID 57050899Methyl 6-fluoro-1,2,3,4-tetrahydro-1-oxo-2-phenyl-2-naphthalenecarboxylate

Produkt 1

HCID 139534336-fluoro-3,4-dihydro-2-phenyl-1(2H)-naphthalenoneAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

The tetralone from Step B (2.8 g, 9.4 mmole) was dissolved in 45 ml of dimethylformamide. To this solution was added lithium chloride (2.0 g, 47 mmole) and water (0.42 ml, 23 mmole). The reaction mixture was heated to 150° C. for 2.5 hrs and then cooled and partitioned between ether and water. The aqueous Phase was separated and extracted three times with ether. The combined organic phases were washed once with water, dried (MgSO4), and concentrated (1.96 g, 87% yield).

Aufarbeitung

  1. temperaturecooled
  2. custompartitioned between ether and water
  3. customThe aqueous Phase was separated
  4. extractionextracted three times with ether
  5. washThe combined organic phases were washed once with water
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated (1.96 g, 87% yield)

Quellen und Nachweise

ORD-Eintrag
ord-c482adfbbac4421e922c5d0c9fb93a29
Quelldatensatz
uspto-grants-1993_01
Patentnummer
US05182303

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