Potassium Carbonate → 3-(4-methoxyphenyl)-4-(4-((6-methylpyridin-2-yl)methoxy)phenyl)furan-2(5H)-one

HRID 446817Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:12][O:11][C:10](=[O:13])[C:9]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([CH3:36])[N:31]=1>CN(C=O)C>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([C:9]2[C:10](=[O:13])[O:11][CH2:12][C:8]=2[C:5]2[CH:4]=[CH:3][C:2]([O:1][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([CH3:36])[N:31]=3)=[CH:7][CH:6]=2)=[CH:15][CH:16]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 4-(4-hydroxyphenyl)-3-(4-methoxyphenyl)furan-2(5H)-one (300 mg, 1.06 mmol) in DMF (10 mL) were added K2CO3 (294 mg, 2.12 mmol), 2-(chloromethyl)-6-methylpyridine (225 mg, 1.59 mol) at RT. The reaction mixture was then heated at 80° C. for 16 h, quenched with ice and then extracted with EtOAc (2×100 mL). The combined organic layers were washed with water, dried over Na2SO4, and concentrated in vacuo to obtain the crude product. The crude material was purified via silica gel column chromatography to afford 3-(4-methoxyphenyl)-4-(4-((6-methylpyridin-2-yl)methoxy)phenyl)furan-2(5H)-one (10 mg) as a solid. 1H NMR (500 MHz, d6-DMSO): δ 8.44 (d, J=7.2 Hz, 1H), 7.79 (m, 1H), 7.71 (d, J=7.6 Hz, 1H), 7.63 (t, J=7.6 Hz, 1H), 7.38-7.27 (m, 3H), 7.16 (d, J=7.2 Hz, 2H), 6.99-6.92 (m, 2H), 5.41 (s, 2H), 5.33 (s, 2H), 2.79 (s, 3H). MS: M+H: m/z=388.2.

Workup

customquenched with ice
extractionextracted with EtOAc (2×100 mL)
washThe combined organic layers were washed with water
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
customto obtain the crude product
customThe crude material was purified via silica gel column chromatography

Sources & evidence

ORD record: ord-f07ee680fdbd48078c82ea987f749b12
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08481534B2

Reaction notes

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