Methyl 4-(bromomethyl)benzoate → 2-(4-Carbomethoxyphenyl)-1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)ethanone

HRID 1728467

Reaktionsgleichung

Reaktionsgleichung von HRID 1728467
[CH3:1][C:2]1([CH3:17])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14](Cl)=[O:15])[CH:5]=[CH:4][C:3]1=2.Br[CH2:19][C:20]1[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][CH:21]=1>C(COC)OC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Zn]>[C:24]([C:23]1[CH:28]=[CH:29][C:20]([CH2:19][C:14]([C:6]2[CH:5]=[CH:4][C:3]3[C:2]([CH3:17])([CH3:1])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]=3[CH:7]=2)=[O:15])=[CH:21][CH:22]=1)([O:26][CH3:27])=[O:25]

Komponenten

6

Edukt 2

HCID 256687Methyl 4-(bromomethyl)benzoateHCID 27954665,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalene-2-carbonyl chloride

Produkt 1

HCID 147264952-(4-Carbomethoxyphenyl)-1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)ethanone

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23994ZincKatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel2×

Versuchsvorschrift

A solution of 4 g (16 mmol) of 5,6,7, 8-tetrahydro-5,5,8,8-tetramethylnaphthalene-2-carbonyl chloride and 4 g (16 mmol) of methyl 4-bromomethylbenzoate in 20 ml of dimethoxyethane was added dropwise to a solution or suspension of 0.56 g of bis(triphenylphosphine)palladium(II) dichloride and 2.1 g of zinc powder in 40 ml of dimethoxyethane at room temperature. The reaction mixture was then refluxed for 6 h. After cooling, solids were filtered off and the filtrate was heated with active carbon and filtered hot. The filtrate was concentrated and yielded after recrystallization 3x from methanol and finally from isopropanol 0.9 g of the title compound of melting point 103°-104° C.

Aufarbeitung

  1. temperatureThe reaction mixture was then refluxed for 6 h
  2. temperatureAfter cooling
  3. filtrationsolids were filtered off
  4. temperaturethe filtrate was heated with active carbon
  5. filtrationfiltered hot
  6. concentrationThe filtrate was concentrated
  7. customyielded
  8. customafter recrystallization 3x from methanol

Quellen und Nachweise

ORD-Eintrag
ord-6a293432ee734933a445f4dd54e81c94
Quelldatensatz
uspto-grants-1994_07
Patentnummer
US05326900

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