5-tert-Butyl-2-(4-methoxy-phenyl)-benzofuran → 4-(5-tert-Butyl-benzofuran-2-yl)-phenol

HRID 1794518Notes

Reaction equation

[C:1]([C:5]1[CH:6]=[CH:7][C:8]2[O:12][C:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19]C)=[CH:15][CH:14]=3)=[CH:10][C:9]=2[CH:21]=1)([CH3:4])([CH3:3])[CH3:2].Cl.N1C=CC=CC=1>O>[C:1]([C:5]1[CH:6]=[CH:7][C:8]2[O:12][C:11]([C:13]3[CH:14]=[CH:15][C:16]([OH:19])=[CH:17][CH:18]=3)=[CH:10][C:9]=2[CH:21]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 200 °C

Procedure

Compound 84 was treated with Pyridine HCl (5 g) and heated to 200° C. After 1 hr, the reaction was cooled and diluted with water. The aqueous layer was extracted with EtOAc, dried over MgSO4, filtered and the crude product was purified by column chromatography (eluant 25% EtOAc/hexanes) to give a solid (0.18 g, 17%); Mp=172–174° C.; 1H NMR (DMSO-d6) δ 9.83 (s, 1 H), 7.70 (d, 2 H, J=8.9 Hz), 7.56 (d, 1 H, J=1.7 Hz), 7.45 (d, 1 H, J=9.0 Hz), 7.32 (dd, 1 H, J=9.0 Hz, 2.1 Hz), 7.11 (s, 1 H), 6.87 (d, 2 H, J=8.5 Hz); MS 265 [M−H]−

Workup

temperaturethe reaction was cooled
extractionThe aqueous layer was extracted with EtOAc
dry with materialdried over MgSO4
filtrationfiltered
customthe crude product was purified by column chromatography (eluant 25% EtOAc/hexanes)

Sources & evidence

ORD record: ord-b9cd899ea475446ebf53eb914bba8a1b
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07022733B2

Reaction notes

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