Potassium Carbonate → 3-(4-methoxyphenyl)-4-(4-(2-(quinolin-2-yl)ethyl)phenyl)furan-2(5H)-one

HRID 446812Notes

Reaction equation

O[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:22]([O-])([O-])=O.[K+].[K+].Cl[CH2:29][C:30]1[CH:39]=[CH:38][C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[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:6]=[CH:7][C:2]([CH2:22][CH2:29][C:30]3[CH:39]=[CH:38][C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[N:31]=3)=[CH:3][CH:4]=2)=[CH:15][CH:16]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred solution of 4-(4-hydroxyphenyl)-3-(4-methoxyphenyl)furan-2(5H)-one (280 mg, 0.99 mol) in DMF (5 mL) were added K2CO3 (274 mg, 1.98 mol) and 2-(chloromethyl)quinoline (255 mg, 1.19 mol) at RT. The reaction mixture was then heated at 80° C. for 3 h, quenched with ice and then extracted with EtOAc (2×20 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 using 20% ethyl acetate in hexanes to afford 3-(4-methoxyphenyl)-4-(4-(2-(quinolin-2-yl)ethyl)phenyl)furan-2(5H)-one (50 mg, 12%) as a yellow solid.

Workup

customquenched with ice
extractionextracted with EtOAc (2×20 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-94e3936b48674afcb55c16afc0d9ea36
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08481534B2

Reaction notes

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