Carbon Dioxide → 5,6-Dihydro-5,5-dimethyl-8-(4-methylphenyl)-2-naphthalenecarboxylic acid

HRID 324220

Reaktionsgleichung

Reaktionsgleichung von HRID 324220
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15](Br)[CH:16]=3)[C:11]([CH3:20])([CH3:19])[CH2:10][CH:9]=2)=[CH:4][CH:3]=1.C([Li])(C)(C)C.[C:26](=[O:28])=[O:27]>C1COCC1>[CH3:19][C:11]1([CH3:20])[CH2:10][CH:9]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=2)[C:17]2[CH:16]=[C:15]([C:26]([OH:28])=[O:27])[CH:14]=[CH:13][C:12]1=2

Komponenten

5

Edukt 3

HCID 280Carbon DioxideHCID 106876226-Bromo-1,1-dimethyl-4-p-tolyl-1,2-dihydronaphthalene2×HCID 178418306HCID 178418306, Verbindung

Produkt 1

HCID 105416825,6-Dihydro-5,5-dimethyl-8-(4-methylphenyl)-2-naphthalenecarboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 3,4-dihydro-1-(4-methylphenyl)-4,4-dimethyl-7-bromonaphthalene (Compound D) (250.0 mg, 0.764 mmol) in 2.0 ml of THF was cooled to −78° C. and 1.0 ml of t-butyllithium (1.68 mmol, 1.7 M solution in pentane) was added slowly. After stirring for 1 hour at −78° C. gaseous CO2 (generated by evaporation of Dry-Ice, and passed though a drying tube) was bubbled through the reaction for 1 hour. The solution was then allowed to warm to room temperature and the reaction was quenched by the addition of 10% HCl. Extraction with EtOAc was followed by washing the combined organic layers with H2O and saturated aqueous NaCl, and drying over MgSO4. Removal of the solvents under reduced pressure and washing of the solid with hexanes afforded the title compound as a colorless solid. 1H NMR (CDCl3): δ 7.94 (1H, dd, J=1.8, 8.1 Hz), 7.76 (1H, d, J=1.8 Hz), 7.45 (1H, d, J=8.1 Hz), 7.24 (4H, m), 6.01 (1H, t, J=4.7 Hz), 2.40 (3H, s), 2.36 (2H, d, J=3. 4.7 Hz), 1.35 (6H, s).

Aufarbeitung

  1. customwas bubbled through the reaction for 1 hour
  2. customthe reaction was quenched by the addition of 10% HCl
  3. extractionExtraction with EtOAc
  4. washby washing the combined organic layers with H2O and saturated aqueous NaCl
  5. dry with materialdrying over MgSO4
  6. customRemoval of the solvents under reduced pressure
  7. washwashing of the solid with hexanes

Quellen und Nachweise

ORD-Eintrag
ord-0f375cbe834e461c8f39217b273c50eb
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06218128B1

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