Methanol → HCID 59264794, compound

HRID 2097242Notes

Reaction equation

C([O-])=O.[NH4+].C([O:12][C:13]1[CH:18]=C(OCC2C=CC=CC=2)[C:16]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:15][C:14]=1[C:33]1[O:37]N=[C:35]([CH3:38])[C:34]=1[C:39]1[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][CH:40]=1)C1C=CC=CC=1.C(OCC)(=O)C.[CH3:53][OH:54]>[Pd]>[OH:54][C:53]1[CH:18]=[C:13]2[C:14]([C:33](=[O:37])[C:34]([C:39]3[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][CH:40]=3)=[C:35]([CH3:38])[O:12]2)=[CH:15][C:16]=1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Ammonium formate (3.2 g, 50 mmol) was added to a solution of 5-(4,6-bis-benzyloxy-biphenyl-3-yl)-4-(4-methoxy-phenyl)-3-methyl-isoxazole (1.4 g, 2.5 mmol) in methanol (20 ml)/ethyl acetate (10 ml) under a nitrogen atmosphere. Palladium on carbon (10%) (cat.) was added and the suspension heated, at 60° C. for ˜18 hrs. The suspension was allowed to cool and ethyl acetate (150 ml) added, and the suspension filtered. The filtrate was washed with water (3×100 ml) and saturated aqueous sodium chloride solution (50 ml). The solution was dried over anhydrous magnesium sulphate and concentrated to give a pale brown gum. Trituration with methanol gave 7-hydroxy-3-(4-methoxy-phenyl)-2-methyl-6-phenyl-chromen-4-one as an off-white solid, dried in vacuo.

Workup

temperatureto cool
filtrationthe suspension filtered
washThe filtrate was washed with water (3×100 ml) and saturated aqueous sodium chloride solution (50 ml)
dry with materialThe solution was dried over anhydrous magnesium sulphate
concentrationconcentrated
customto give a pale brown gum

Sources & evidence

ORD record: ord-e70608ac207648c5805966d4fb576156
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08450310B2

Reaction notes

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