Acetovanillone → (E)-1,5-bis-(4-hydroxy-3-methoxyphenyl)-pent-4-ene-1,3-dione

HRID 733291Notes

Reaction equation

HRID 733291 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:13])[CH2:9][C:10](=[O:12])[CH3:11])=[CH:4][C:3]=1[O:14][CH3:15].C[C:17]([C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[C:21]([O:26][CH3:27])[CH:20]=1)=O.[H-].[Na+].CC(C)(C)C(=O)CC(=O)C>C(OCC)(=O)C>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:13])[CH2:9][C:10](=[O:12])/[CH:11]=[CH:17]/[C:19]2[CH:24]=[CH:23][C:22]([OH:25])=[C:21]([O:26][CH3:27])[CH:20]=2)=[CH:4][C:3]=1[O:14][CH3:15]

Participants

6

Reactant 4

HCID 2214AcetovanilloneHCID 24758Sodium hydrideHCID 817415,5-Dimethylhexane-2,4-dioneHCID 102360841-(4-Hydroxy-3-methoxyphenyl)-butane-1,3-dione

Product 1

HCID 68815772(E)-1,5-bis-(4-hydroxy-3-methoxyphenyl)-pent-4-ene-1,3-dioneYield 39%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

By a similar procedure as described in Example 1 using 1-(4-hydroxy-3-methoxyphenyl)-butane-1,3-dione (prepared by reaction of 4-hydroxy-3-methoxyacetophenone with ethyl acetate in the presence of sodium hydride) in place of 5,5-dimethylhexane-2,4-dione, (E)-1,5-bis-(4-hydroxy-3-methoxyphenyl)-pent-4-ene-1,3-dione (920 mg, 39%) was obtained as yellow needles: mp 170-172° C.; LRMS m/z 342 (M+); 1H NMR (500 MHz, CDCl3) δ 3.95 (3H, s, OCH3), 3.98 (3H, s, OCH3), 5.85 (1H, brs, OH), 6.04 (1H, brs, OH), 6.26 (1H, s, H-2), 6.48 (1H, d, J=15.7 Hz, H-4), 6.94 (1H, d, J=7.2 Hz, H-5″), 6.97 (1H, d, J=8.3 Hz, H-5′), 7.05 (1H, brs, H-2″), 7.12 (1H, brd, J=8.3 Hz, H-6″), 7.51 (1H, brd, J=7.2 Hz, H-6′), 7.56 (1H, brs, H-2′), 7.60 (1H, J=15.7 Hz, H-5), 16.2 (1H, brs, OH) ppm; TLC Rf=0.5 (silica, dichloromethane); HPLC Rt 14 min 99.6% purity.

Sources & evidence

ORD record
ord-e14fda0c702f40a790e96abf57e587ab
Source dataset
uspto-grants-2009_09
Patent number
US07589123B2

Reaction notes

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