Benzene → (+/-) Ethyl (E)-4-[2-(5,6,7,8-Tetrahydro-5.5-dimethyl-8-hydroxy-8-(methylcarbethoxy)naphthalen-2-yl)ethenyl]benzoate

HRID 992111

Reaktionsgleichung

Reaktionsgleichung von HRID 992111
[CH3:1][C:2]1([CH3:26])[CH2:11][CH2:10][C:9](=[O:12])[C:8]2[CH:7]=[C:6](/[CH:13]=[CH:14]/[C:15]3[CH:25]=[CH:24][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17][CH:16]=3)[CH:5]=[CH:4][C:3]1=2.BrC[C:29]([O:31][CH2:32][CH3:33])=[O:30].[CH:34]1C=CC=CC=1>[Zn]>[CH3:26][C:2]1([CH3:1])[CH2:11][CH2:10][C:9]([OH:12])([C:29]([O:31][CH2:32][CH2:33][CH3:34])=[O:30])[C:8]2[CH:7]=[C:6](/[CH:13]=[CH:14]/[C:15]3[CH:16]=[CH:17][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:24][CH:25]=3)[CH:5]=[CH:4][C:3]1=2

Komponenten

5

Edukt 3

HCID 241Benzene2×HCID 7748Ethyl bromoacetateHCID 12069038Ethyl (E)-4-[2-(5,6,7,8-tetrahydro-5,5-dimethyl-8-oxo-2-naphthalenyl)ethenyl]-benzoate2×

Produkt 1

HCID 86586453(+/-) Ethyl (E)-4-[2-(5,6,7,8-Tetrahydro-5.5-dimethyl-8-hydroxy-8-(methylcarbethoxy)naphthalen-2-yl)ethenyl]benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23994ZincKatalysator

Versuchsvorschrift

To a refluxing solution of 0.75 g (11.5 mmol) of granular zinc in 5.0 mL of benzene was added a solution of ethyl (E)-4-[2-(5,5-dimethyl-5,6,-dihydro-naphthalen-8(7H)-one-2-yl)ethenyl]-benzoate (Compound A2) in 5.0 mL of benzene followed by 0.27 g (0.18 mmol) of ethyl bromoacetate. The resulting mixture was refluxed for 24 h. The reaction was cooled, filtered through celite. The filtrate was washed with 10% HCl, sat. aqueous NaHCO3 and brine. The organic phase was dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica, 10% ethyl acetate in hexane) to afford the title compound as a white solid.

Aufarbeitung

  1. temperatureThe resulting mixture was refluxed for 24 h
  2. temperatureThe reaction was cooled
  3. filtrationfiltered through celite
  4. washThe filtrate was washed with 10% HCl, sat. aqueous NaHCO3 and brine
  5. dry with materialThe organic phase was dried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified by flash chromatography (silica, 10% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-fa5ef8de68b5476b870edbccd9551e31
Quelldatensatz
uspto-grants-2002_10
Patentnummer
US06465663B2

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