Methanol → 4-[(4,4-Dimethyl-2-isopropoxy-3,4-dihydro-7-quinolinyl)ethynyl]benzoic acid

반응식

[CH3:1][C:2]1([CH3:18])[C:11]2[C:6](=[CH:7][C:8]([C:12]#[CH:13])=[CH:9][CH:10]=2)[NH:5][CH:4]([O:14][CH:15]([CH3:17])[CH3:16])[CH2:3]1.[Li+].[OH-:20].[CH3:21][OH:22]>O1CCCC1>[CH3:1][C:2]1([CH3:18])[C:11]2[C:6](=[CH:7][C:8]([C:12]#[C:13][C:6]3[CH:11]=[CH:10][C:9]([C:21]([OH:22])=[O:20])=[CH:8][CH:7]=3)=[CH:9][CH:10]=2)[N:5]=[C:4]([O:14][CH:15]([CH3:16])[CH3:17])[CH2:3]1

참가 물질

실험 절차

To a solution of 0.0586 g (0.15 mmol) of 4,4-dimethyl-2-iso-propoxy-1,2,3,4-tetrahydro-7-ethynylquinoline (Compound 27) in 3.0 ml of tetrahydrofuran were added 1.0 ml (1.1 mmol) of 1.1M aqueous LiOH and 1.0 ml of methanol. The resulting solution was stirred at room temperature for 2 h. The reaction mixture was then concentrated and water was added to the residue. The aqueous layer was acidified to pH=1 with 10% HCl, and extracted with diethyl ether (2×). The organic layers were dried (MgSO4), filtered and concentrated to give the title compound as a solid.