(4-(Phenylmethoxy)phenoxy)acetic acid → HCID 16735552, compound

HRID 386427Notes

Reaction equation

HRID 386427 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]=1

Participants

3

Reactant 2

HCID 563696(4-(Phenylmethoxy)phenoxy)acetic acidHCID 7371945-(2-Pyridyl)oxazole

Product 1

HCID 16735552HCID 16735552, compoundYield 10%

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).

Sources & evidence

ORD record
ord-d488976ce27b4538bb821c75dfc4d31b
Source dataset
uspto-grants-2013_02
Patent number
US08372823B2

Reaction notes

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