Sodium hydride → 4-Chloro-6-methyl-11h-5-oxa-10-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid methyl ester
Reaktionsgleichung
[H-].[Na+].[CH3:3][O:4][C:5](=[O:24])[C:6]1[CH:11]=[C:10]([CH3:12])[C:9](Br)=[C:8]([S:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[C:17]=2[OH:23])[CH:7]=1>CN(C=O)C>[CH3:3][O:4][C:5]([C:6]1[CH:11]=[C:10]([CH3:12])[C:9]2[O:23][C:17]3[C:18]([Cl:22])=[CH:19][CH:20]=[CH:21][C:16]=3[CH2:15][S:14][C:8]=2[CH:7]=1)=[O:24]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 80 °C
Versuchsvorschrift
Sodium hydride (1.65 g, 0.068 mol) was added portionwise to a solution of compound of Example 15a (23 g, 0.057 mol) in DMF (600 mL) and stirred at 80° C. for 10 h. The solvent was removed, and chloroform (300 mL) was added. The organic layer was washed with 10% HCl (2×80 mL), followed by water (100 mL), and brine and dried over anhydrous sodium sulphate. The solvent was removed and the crude product obtained was purified by column chromatography (silica gel, ethyl acetate/pet ether) to obtain the title compound. Yield: 9 g, (49%); 1H NMR (CDCl3, 300 MHz): δ 2.50 (s, 3H, CH3), 3.91 (s, 3H, OCH3), 4.21 (s, 2H, CH2), 7.05 (m, 2H, Ar), 7.28 (d, 1H, Ar), 7.60 (d, 2H, Ar); MS: m/e (El) 320 (M+).
Aufarbeitung
- customThe solvent was removed
- additionchloroform (300 mL) was added
- washThe organic layer was washed with 10% HCl (2×80 mL)
- dry with materialdried over anhydrous sodium sulphate
- customThe solvent was removed
- customthe crude product obtained
- customwas purified by column chromatography (silica gel, ethyl acetate/pet ether)
Quellen und Nachweise
- ORD-Eintrag
- ord-6933704032b4413d848ed23159a09fe2
- Quelldatensatz
- uspto-grants-2012_04
- Patentnummer
- US08163730B2
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