6-Methoxy-alpha-tetralone → 6-Methoxy-2-[4-(methylsulfanyl)phenyl]naphthalen-1-ol

HRID 748916Notes

Reaction equation

HRID 748916 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[CH2:8][CH2:7][CH2:6]2.Br[C:15]1[CH:20]=[CH:19][C:18]([S:21][CH3:22])=[CH:17][CH:16]=1.CC(C)([O-])C.[Na+].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([OH:13])=[C:8]([C:15]1[CH:20]=[CH:19][C:18]([S:21][CH3:22])=[CH:17][CH:16]=1)[CH:7]=[CH:6]2

Participants

7

Reactant 4

HCID 141126-Methoxy-alpha-tetraloneHCID 660374-BromothioanisoleHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxide

Product 1

HCID 685188176-Methoxy-2-[4-(methylsulfanyl)phenyl]naphthalen-1-olYield 15.1%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

Heat a solution of 6-methoxytetralone (9.6 g, 54 mmol), 4-bromothioanisole (25 mL, 123 mmol), sodium tert-butoxide (20.9 g, 217 mmol), palladium (II) acetate (610 mg, 2.72 mmol), racemic 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (1.8 g, 2.72 mmol) and toluene (150 mL) at reflux for 18 hours, then cool to ambient temperature and evaporate to dryness under reduced pressure. Dissolve the residue in dichloromethane and wash with aqueous hydrochloric acid (1N), filter through celite and chromatograph twice on silica gel with hexane/ethyl acetate mixtures to give 2.41 g of 6-methoxy-2-(4-methylsulfanyl-phenyl)-naphthalen-1-ol (15%).

Workup

  1. temperatureat reflux for 18 hours
  2. customevaporate to dryness under reduced pressure
  3. dissolutionDissolve the residue in dichloromethane
  4. washwash with aqueous hydrochloric acid (1N)
  5. filtrationfilter through celite and chromatograph twice on silica gel with hexane/ethyl acetate

Sources & evidence

ORD record
ord-08be2b948640445c9b6ba5e76f482e00
Source dataset
uspto-grants-2008_07
Patent number
US07399867B2

Reaction notes

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