Hydrochloric Acid → 6-Methoxy-2-[4-(methylsulfanyl)phenyl]naphthalen-1-ol

HRID 732830ノート

反応式

HRID 732830 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.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2N(C)C)CCCCC1.CC(C)([O-])C.[Na+].Cl>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O1CCCC1.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

9

反応物 5

HCID 313Hydrochloric AcidHCID 141126-Methoxy-alpha-tetraloneHCID 660374-BromothioanisoleHCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 23676156Sodium t-butoxide

生成物 1

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

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Place 6-methoxy-1-tetralone (1 eq.), 4-bromothioanisole (2.5 eq.), palladium acetate (0.01 eq.), 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl (0.02 eq.) and toluene in a 3 neck flask equipped with a mechanical stirrer, reflux condenser, nitrogen purge and a temperature probe. Add sodium tert-butoxide (4 eq.) and heat the slurry to reflux. After about 2-4 hours, cool the reaction to room temperature and add 3M aqueous HCl along with tetrahydrofuran. Stir the biphasic reaction mixture for 30 minutes before filtration and separation of the layers. Concentrate the organic layer to isolate 6-methoxy-2-(4-methylthiophenyl)naphthalene-1-ol by filtration.

後処理

  1. temperaturereflux condenser
  2. customnitrogen purge
  3. temperatureto reflux
  4. temperaturecool
  5. customthe reaction to room temperature
  6. customthe biphasic reaction mixture for 30 minutes
  7. filtrationbefore filtration and separation of the layers
  8. concentrationConcentrate the organic layer

出典と根拠

ORDレコード
ord-26de4d369cb74903adda9276724dd92a
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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