Vertellus → 3-Methyl-2-phenyl-1-naphthalenol

HRID 1992986Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1992986
CC1C=CC(S(O[C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][C:16]([CH3:29])=[C:17]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[C:18]=3[OH:22])[CH:13]=2)(=O)=O)=CC=1.[B-].[Na+]>C(Cl)(Cl)Cl.CO.O.O.O.O.O.O.[Ni](Cl)Cl>[CH3:29][C:16]1[C:17]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:18]([OH:22])[C:19]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:21][CH:20]=2

Komponenten

6

Edukt 2

HCID 22959485VertellusHCID 866166715-Hydroxy-7-methyl-6-phenyl-2-naphthalenyl 4-methylbenzenesulfonate

Produkt 1

HCID 685367573-Methyl-2-phenyl-1-naphthalenolAusbeute 44,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11791229Dichloronickel;hexahydrateKatalysatorHCID 887MethanolLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

To a cold (5° C.) solution of 5-hydroxy-7-methyl-6-phenyl-2-naphthalenyl 4-methylbenzenesulfonate (239) (0.250 g, 0.62 mmol) in CHCl3 (5 mL) and MeOH (5 mL) was added nickel chloride hexahydrate (0.238 g, 1.24 mmol). To the above mixture sodium borohydrate (0.471 g, 12.4 mmol) was added portion-wise. The resulting black mixture was stirred at that temperature for 15 min. Reaction mixture was filtered through a pad of celite (washings were done with CHCl3). The filtrate was concentrated under reduced pressure to afford the crude product. The product was purified by column chromatography to afford 0.064 g (44%) of the title compound (86) as an oil. 1H NMR (400 MHz, CDCl3): δ 8.22 (d, J=8.0 Hz, 1H), 7.77 (d, J=8.0 Hz, 1H), 7.59-7.55 (m, 2H), 7.52-7.46 (m, 3H), 7.40-7.36 (m, 3H), 5.28 (s, 1H), 2.22 (s, 3H). LCMS (ESI) m/z (M+H)+.

Aufarbeitung

  1. customReaction mixture
  2. filtrationwas filtered through a pad of celite (washings were done with CHCl3)
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customto afford the crude product
  5. customThe product was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-f6db188b19c94520a5a43a3ffbbe77a0
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07649093B2

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