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Hydrochloric Acid → 2-Acetyl-8,8-dimethyl-5,6,7,8-tetrahydronaphthalene

HRID 1453627
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1453627
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][C:9]2([CH3:13])[CH3:12])=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:19]([O:21]CC)=[CH2:20])CCC.Cl>C1COCC1.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>[CH3:12][C:9]1([CH3:13])[C:10]2[CH:11]=[C:2]([C:19](=[O:21])[CH3:20])[CH:3]=[CH:4][C:5]=2[CH2:6][CH2:7][CH2:8]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 105379407-Bromo-1,1-dimethyl-1,2,3,4-tetrahydronaphthalene2×

Produkt 1

HCID 197480082-Acetyl-8,8-dimethyl-5,6,7,8-tetrahydronaphthaleneAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476
HCID 178418476, Verbindung
Katalysator
HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A solution of 7-bromo-1,1-dimethyl-1,2,3,4-tetrahydro-naphthalene (Compound 15, 1.20 g, 5.94 mmol) in 20 ml of THF was first degassed by bubbling with argon for 30 min. Tributyl(1-ethoxyvinyl)tin (4.29 g, 11.88 mmol) and PdCl2(PPh3)2 (422 mg, 0.60 mmol) were added. After stirring at 80° C. for 18 h, the mixture was cooled to room temperature and 3 mL of 10 % HCl was added. The mixture was then stirred for another 30 min, then extracted with ethyl acetate (3×10 mL). The combined organic layer was washed with brine (1×10 mL), dried (MgSO4) and concentrated at reduced pressure. Purification by flash chromatography (80:20 hexane/ethyl acetate) afforded the title compound (669 mg, 56% yield) as a colorless oil:

Aufarbeitung

  1. customby bubbling with argon for 30 min
  2. temperaturethe mixture was cooled to room temperature
  3. stirringThe mixture was then stirred for another 30 min
  4. extractionextracted with ethyl acetate (3×10 mL)
  5. washThe combined organic layer was washed with brine (1×10 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated at reduced pressure
  8. customPurification by flash chromatography (80:20 hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-b532222ba5e2412ab94f1e8be79c8652
Quelldatensatz
uspto-grants-2009_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07476673B2

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