Acetic Acid → (E)-4-{3-[(E)-2-(7-Chloro-quinolin-2-yl)-vinyl]-phenyl}-but-3-en-2-one

反応式

[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](/[CH:12]=[CH:13]/[C:14]3[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=3)[CH:17]=O)=[N:9]2)=[CH:4][CH:3]=1.[OH-].[Na+].C(O)(=O)C.[CH3:28][C:29]([CH3:31])=[O:30].C1COCC1>>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](/[CH:12]=[CH:13]/[C:14]3[CH:15]=[C:16](/[CH:17]=[CH:28]/[C:29](=[O:30])[CH3:31])[CH:19]=[CH:20][CH:21]=3)=[N:9]2)=[CH:4][CH:3]=1

参加物

反応物 4

HCID 176Acetic Acid

HCID 14798Sodium Hydroxide

HCID 100173053-[(E)-2-(7-Chloroquinolin-2-yl)ethenyl]benzaldehyde

HCID 22559816Acetone tetrahydrofuran

生成物 1

HCID 86720741(E)-4-{3-[(E)-2-(7-Chloro-quinolin-2-yl)-vinyl]-phenyl}-but-3-en-2-one収率 76.47%

実験手順

To a solution of aldehyde 29 (15 g, 0.0519 mol) in a mixture of 200 ml of Acetone:THF (1:1) was added 10% aq. NaOH solution and stirred for 3 hours. Dilute acetic acid was added till pH of mixture was acidic. The reaction mixture was evaporated to half volume and poured into water (200 ml). The solid separated out was filtered to yield (E)-4-{3-[(E)-2-(7-Chloro-quinolin-2-yl)-vinyl]-phenyl}-but-3-en-2-one (13 g, 76.47%) as a yellow solid.