Water → 3'-[(E)-2-[4-(4-Phenylbutoxy)phenyl]ethen-1-yl]-2'-hydroxyacetophenone

HRID 1603928Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4-(4-phenylbutoxy)styrene (742 mg, 2.92 mmol), 2'-hydroxy-3'-iodoacetophenone (612 mg, 2.33 mmol), triethylamine (0.408 ml, 3.01 mmol), palladium (II) acetate (14 mg, 0.06 mmol) in acetonitrile (15 ml) was left under stirring at 100° C. for 24 h. Then the mixture was added with water (15 ml), extracted with ethyl ether (4×30 ml), dried and the solvents were evaporated off under reduced pressure. The resulting residue was purified by chromatography through a silica gel column, eluting with petroleum ether:ethyl ether, 9:1, recovering 633 g of the title compound (70% yield).

Workup

waitwas left
extractionextracted with ethyl ether (4×30 ml)
customdried
customthe solvents were evaporated off under reduced pressure
customThe resulting residue was purified by chromatography through a silica gel column
washeluting with petroleum ether

Sources & evidence

ORD record: ord-4e44a95fd28c4f1db71e4d09a2b77f36
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05990142

Reaction notes

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