Carbon Dioxide → 1-(Tol-4-yl)3,4-dihydro-4,4-dimethyl-7-naphthaldehyde

HRID 2605

Reaktionsgleichung

Reaktionsgleichung von HRID 2605
[C:1]1([CH3:20])[CH:6]=[CH:5][C:4]([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14](Br)[CH:15]=3)[C:10]([CH3:19])([CH3:18])[CH2:9][CH:8]=2)=[CH:3][CH:2]=1.[Li]C(C)(C)C.CCCCC.CN(C)[CH:33]=[O:34].C(=O)=O>C1COCC1.C(OC(=O)C)C>[C:1]1([CH3:20])[CH:6]=[CH:5][C:4]([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([CH:33]=[O:34])[CH:15]=3)[C:10]([CH3:19])([CH3:18])[CH2:9][CH:8]=2)=[CH:3][CH:2]=1

Komponenten

8

Edukt 5

HCID 280Carbon DioxideHCID 6228DimethylformamideHCID 8003PentaneHCID 106876226-Bromo-1,1-dimethyl-4-p-tolyl-1,2-dihydronaphthalene2×HCID 178418306HCID 178418306, Verbindung

Produkt 1

HCID 865886771-(Tol-4-yl)3,4-dihydro-4,4-dimethyl-7-naphthaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a cold (-78° C.), stirred solution of 1-(tol-4-yl)3,4-dihydro-4,4-dimethyl-7-bromo-naphthalene (Compound B 1 g, 3.2 mmol), in THF (17 mL) was added t-BuLi in pentane (1.7M solution, 3 mL, 5.1 mmol). After 10 minutes dry dimethylformamide (DMF) (600 mg, 8 mmol) was added and the dry-ice cooling was replaced with ice-water bath. The mixture was gradually warmed to ambient temperature and diluted with ethylacetate (150 mL), washed with water (15 mL). The organic layer was dried with MgSO4 and solvent was removed under reduced pressure. The crude material was purified by silicagel chromatography to afford the title compound as a white solid.

Aufarbeitung

  1. washwashed with water (15 mL)
  2. dry with materialThe organic layer was dried with MgSO4 and solvent
  3. customwas removed under reduced pressure
  4. customThe crude material was purified by silicagel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-bf0cea00f0c14b87bedbeafd627d9061
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05728846

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