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

HRID 22196Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 22196
[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). 1H NMR (CDCl3) δ: 8.13 (1H, dd, J=6,10 Hz), 7.31 (5H, m) 6.99 (2H, m), 3.80 (1H, m), 3.07 (2H, m), 2.43 (2H, m).

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-6ff7a09fc901415cac37fb3dec45b7b5
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05428027

Notizen zur Reaktion

Wird geladen…