Triphenylphosphine → 3,4-dihydro-6-methylnaphthalen-1(2H)-one

HRID 1049622

Reaktionsgleichung

Reaktionsgleichung von HRID 1049622
Br[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.[CH3:13]B(O)O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1COCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:13][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

7

Edukt 4

HCID 11776TriphenylphosphineHCID 62657Potassium Phosphate, TribasicHCID 139377Methylboronic AcidHCID 101050696-Bromo-1-tetralone

Produkt 1

HCID 1626203,4-dihydro-6-methylnaphthalen-1(2H)-oneAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 19 (1.4 g, 6.1 mmol), methyl boronic acid (0.6 g, 9.3 mmol), Pd(OAc)2 (0.07 g, 0.31 mmol), PPh3 (0.16 g, 0.61 mmol), and K3PO4 (5.2 g, 24 mmol) in dry THF were stirred at reflux under N2 atm overnight. After cooling at room temperature, crude was filtered through celite, concentrated by rotary evaporation, and purified by column chromatography to give 6-methyl-3,4-dihydronaphthalen-1(2H)-one (20) (88%). 1H NMR (600 MHz, CDCl3) δ 7.93 (d, J=12.0 Hz, 1H), 7.11 (d, J=12.0 Hz, 1H), 7.06 (s, 1H), 2.92 (t, J=6.0 Hz, 2H), 2.63 (t, J=12.0 Hz, 2H), 2.37 (s, 3H), 2.13-2.10 (m, 2H). GC-MS (ES) for C11H12O [M]+ 160.

Aufarbeitung

  1. temperatureat reflux under N2 atm overnight
  2. filtrationcrude was filtered through celite
  3. concentrationconcentrated by rotary evaporation
  4. custompurified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d605d5ded35a41ffab5dceefbd1d25c7
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09382245B2

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