HCID 86618198, compound → 7-(2-Hydroxy-3-phenylpropoxy)-3-(4-methoxyphenyl)chromen-4-one

HRID 1694662Notes

Reaction equation

[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[C:26](=[O:27])[C:25]3[C:20](=[CH:21][C:22]([O:28][CH2:29][CH:30]4[CH2:32][O:31]4)=[CH:23][CH:24]=3)[O:19][CH:18]=2)=[CH:13][CH:12]=1>O1CCCC1>[OH:31][CH:30]([CH2:32][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH2:29][O:28][C:22]1[CH:21]=[C:20]2[C:25]([C:26](=[O:27])[C:17]([C:14]3[CH:15]=[CH:16][C:11]([O:10][CH3:9])=[CH:12][CH:13]=3)=[CH:18][O:19]2)=[CH:24][CH:23]=1

Participants

Conditions

Temperature: -40 °C

Procedure

To a solution of cuprous iodide (0.14 g, 0.74 mmol) in tetrahydrofuran (2 ml) was added phenylmagnesium bromide in tetrahydrofuran (1M, 2.22 ml, 2.22 mmol) dropwise at −40° C. After 5 minutes 3-(4-methoxyphenyl)-7-(oxiran-2-ylmethoxy)chromen-4-one (0.24 g, 0.74 mmol) in tetrahydrofuran (4 ml) was added slowly, and stirred at −40° C. for 1 hour. The mixture was quenched with saturated ammonium chloride and water, extracted with ethyl acetate, the organic layer washed with brine, dried over sodium sulfate, and the solvent removed under reduced pressure. The residue was purified by preparative thin layer chromatography, eluting with 10% methanol/methylene chloride, followed by ethyl acetate/hexane 2/3, to provide 7-(2-hydroxy-3-phenylpropoxy)-3-(4-methoxyphenyl)chromen-4-one.

Workup

customThe mixture was quenched with saturated ammonium chloride and water
extractionextracted with ethyl acetate
washthe organic layer washed with brine
dry with materialdried over sodium sulfate
customthe solvent removed under reduced pressure
customThe residue was purified by preparative thin layer chromatography
washeluting with 10% methanol/methylene chloride

Sources & evidence

ORD record: ord-2862fde44e37486ba03fe1aa1edac50a
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08158810B2

Reaction notes

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