Hydrochloric Acid → 3-[4-(2-Methyl-quinolin-4-ylmethoxy)-phenyl]-4,5-dihydro-isoxazole-5-carbaldehyde
Reaction equation
C[O:2][CH:3](OC)[CH:4]1[O:8][N:7]=[C:6]([C:9]2[CH:27]=[CH:26][C:12]([O:13][CH2:14][C:15]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[N:18]=[C:17]([CH3:25])[CH:16]=3)=[CH:11][CH:10]=2)[CH2:5]1.Cl>C1COCC1>[CH3:25][C:17]1[CH:16]=[C:15]([CH2:14][O:13][C:12]2[CH:26]=[CH:27][C:9]([C:6]3[CH2:5][CH:4]([CH:3]=[O:2])[O:8][N:7]=3)=[CH:10][CH:11]=2)[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
The product from step 10a (0.4 g, 1.0 mmol) was dissolved in THF (5 mL) and 6 N HCl (5 mL) and heated to 60° C. for 2.5 h. The reaction was cooled and concentrated, and the aqueous layer was neutralized with NaOH and then extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated to give an oil. The oil was purified with FCC eluting ethyl acetate:methylene chloride (80:20) to give 3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-4,5-dihydro-isoxazole-5-carbaldehyde (0.1 g, 72%) as an oil. MS found: (M+H)+=347.