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

HRID 1992986Notes

Reaction equation

HRID 1992986 reaction equation
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

Participants

6

Reactant 2

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

Product 1

HCID 685367573-Methyl-2-phenyl-1-naphthalenolYield 44.1%

Reagents, catalysts & solvents 3

HCID 11791229Dichloronickel;hexahydrateCatalystHCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-f6db188b19c94520a5a43a3ffbbe77a0
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

Loading…