Ethyl Acetate → (E)-4-(4-Benzyl-phenyl)-1-[5-(4-bromo-phenyl)-3-methyl-isoxazol-4-yl]-but-3-en-1-ol

HRID 1183324Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[C:9]=2[CH:14]([OH:18])[CH2:15][CH:16]=[CH2:17])=[CH:4][CH:3]=1.[CH2:19]([C:26]1[CH:31]=[CH:30][C:29](I)=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CCOC(C)=O>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:19]([C:20]1[CH:25]=[CH:24][C:23](/[CH:17]=[CH:16]/[CH2:15][CH:14]([C:9]2[C:10]([CH3:13])=[N:11][O:12][C:8]=2[C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=2)[OH:18])=[CH:22][CH:21]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

Conditions

Temperature: 85 °C

Procedure

1-[5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]-but-3-en-1-ol (0.380 g, 1.233 mmol) in acetonitrile (4 mL) was added to a flask containing 1-benzyl-4-iodo-benzene (0.3649 g, 1.233 mmol) and cesium carbonate (0.4102 g, 1.233 mmol). Palladium(II) acetate (0.030 g, 0.1233 mmol) was added and the reaction was heated to 85° C. and stirred overnight. The reaction was then cooled and submitted to standard aqueous workup followed by silica gel chromatography (0-50% EtOAc in hexanes) to yield the title compound.

Workup

temperatureThe reaction was then cooled

Sources & evidence

ORD record: ord-38caf3175f0e433ca76b86cece30a3fc
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08664220B2

Reaction notes

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