Diethyl Ether → HCID 22247291, 화합물

반응식

[Al].[Li].[H-].[Cl-].[Al+3].[Cl-].[Cl-].[CH3:8][C:9]1[CH:18]=[C:17]([CH3:19])[CH:16]=[C:15]2[C:10]=1[CH:11]=[CH:12][C:13](=O)[NH:14]2.[CH3:21][CH2:22][O:23]CC>>[C:22]([N:14]1[C:15]2[C:10](=[C:9]([CH3:8])[CH:18]=[C:17]([CH3:19])[CH:16]=2)[CH2:11][CH2:12][CH2:13]1)(=[O:23])[CH3:21]

참가 물질

반응물 5

HCID 3283Diethyl Ether2회

HCID 166653Hydride

HCID 6451240Aluminum(III) Chloride

HCID 16211445Aluminum;lithium

HCID 22247325154205-24-0

생성물 1

HCID 22247291HCID 22247291, 화합물

실험 절차

Lithium aluminum. hydride (687 mg) was suspended in ether (16 ml), and aluminum chloride (4.2 g) was added. A solution of 5,7-dimethylquinolone (1.6 g) in ether (16 ml) was dropwise added and the mixture was refluxed for 0.5 hr. The reaction mixture was poured into ice water (100 ml) and extracted with chloroform (100 ml). After washing with water, the chloroform layer was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The obtained 5,7dimethyl-1,2,3,4-tetrahydroquinoline was dissolved in chloroform (30 ml), and acetic anhydride (929 mg) was added, which was followed by stirring at room temperature for 1 hr. Chloroform (100 ml) was added to the reaction mixture, and the mixture was washed successively with saturated aqueous solution of sodium hydrogencarbonate and water and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: ethyl acetate/benzene=1/5−1/1) to give 1.5 g of oily 1-acetyl-5,7-dimethyl-1,2,3,4-tetrahydroquinoline.