Reaktion #2080168

Reaktionsgleichung

5-hydroxy-7-methyl-6-phenyl-2-naphthalenyl 4-methylbenzenesulfonate

sodium borohydrate

→

title compound ( 86 )

Ausbeute 44.1%

3-methyl-2-phenyl-1-naphthalenol

Ausbeute 44.1%

Lösungsmittel

CHCl3

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeReaction mixture
2. 2
   Filtrationwas filtered through a pad of celite (washings were done with CHCl3)
3. 3
   EinengenThe filtrate was concentrated under reduced pressure
4. 4
   Sonstigeto afford the crude product
5. 5
   SonstigeThe product was purified by column chromatography

Vorschrift

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)+.

Quelle