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

HRID 732782ノート

反応式

HRID 732782 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 1140Toluene溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-7c5de744b5fb471ca23761b331217ab2
出典データセット
uspto-grants-2009_09
特許番号
US07585977B2

反応ノート

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