(4-(Phenylmethoxy)phenoxy)acetic acid → 2-(4-(Benzyloxy)phenoxy)-1-(5-(pyridin-2-yl)oxazol-2-yl)ethanone
Reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[O:11][CH:10]=[N:9][CH:8]=1.[CH2:12]([O:19][C:20]1[CH:30]=[CH:29][C:23]([O:24][CH2:25][C:26](O)=[O:27])=[CH:22][CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[CH2:12]([O:19][C:20]1[CH:21]=[CH:22][C:23]([O:24][CH2:25][C:26]([C:10]2[O:11][C:7]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)=[CH:8][N:9]=2)=[O:27])=[CH:29][CH:30]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1Participants
3
Procedure
The title compound was prepared from 5-(2-pyridyl)oxazole and 2-(4-(benzyloxy)phenoxy)acetic acid (commercially available) using General Procedure B. Column chromatography (SiO2, 2.5×6 cm, 20-40% EtOAc-hexanes gradient) followed by PTLC (SiO2, 50% EtOAc-hexanes) afforded 11b (35 mg, 0.09 mmol, 10%) as a pale yellow solid: 1H NMR (CDCl3, 500 MHz) 8.70 (app d, 1H, J=4.0 Hz), 8.04 (d, 1H, J=8.1 Hz), 7.86 (td, 1H, J=7.7, 1.5 Hz), 7.55-7.52 (m, 1H), 7.44-7.33 (m, 6H), 6.94-6.89 (m, 4H), 5.45 (s, 2H), 5.03 (s, 2H); ESI-TOF m/z 387.1343 (C23H19N2O4+H+ requires 387.1345).