Reaktionsgleichung
CC1[S:6][C:5]([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14](Br)[CH:15]=3)[C:10]([CH3:19])(C)[CH2:9][CH:8]=2)=CC=1.[Li][C:21](C)(C)[CH3:22].[CH3:25]CCCC.CN([CH:33]=[O:34])C.C(=O)=O.[CH2:38]1[CH2:42]O[CH2:40][CH2:39]1>CCOCC>[CH3:40][C:39]1[S:6][C:5]([C:7]2[C:16]3[C:11](=[CH:10][CH:19]=[C:25]([CH:33]=[O:34])[CH:15]=3)[C:12]([CH2:13][CH3:14])([CH2:21][CH3:22])[CH2:9][CH:8]=2)=[CH:42][CH:38]=1Komponenten
8
Edukt 6
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a cold (−78° C.) solution of 1-(5-methyl-thien-2-yl)-3,4-dihydro-4,4-dimethyl-7-bromo-naphthalene (Compound F, 1.35 g, 4.1 mmol), in THF (20 mL) was added t-BuLi in pentane (1.7M solution, 3.5 mL, 5.95 mmol). The reaction was stirred for 15 minutes. and DMF (600 mg, 5.8 mmol) was added and dry-ice cooling was replaced with ice-water bath. The mixture was stirred at ambient temperature for 4 hours. The reaction mixture was diluted with ether (70 mL) and washed with water (5 mL), brine (5 mL) and dried with MgSO4. Solvent was removed by distillation. The product was purified by silicagel chromatography to afford the title compound as a colorless oil.
Aufarbeitung
- stirringThe mixture was stirred at ambient temperature for 4 hours
- washwashed with water (5 mL), brine (5 mL)
- dry with materialdried with MgSO4
- customSolvent was removed by distillation
- customThe product was purified by silicagel chromatography
Quellen und Nachweise
- ORD-Eintrag
- ord-0dfef76ef84349f897b21b46838ad55b
- Quelldatensatz
- uspto-grants-2007_01
- Patentnummer
- US07166726B2
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