Sodium hydride → (E)-5-(4-hydroxy-3-methoxyphenyl)-1-(4-iodophenyl)-pent-4-ene-1,3-dione

HRID 733292Notes

Reaction equation

HRID 733292 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:13])[CH2:9][C:10](=[O:12])[CH3:11])=[CH:4][CH:3]=1.C[C:15](C1C=CC(I)=CC=1)=[O:16].[H-].[Na+].C[C:27]([CH3:35])([CH3:34])[C:28](=O)[CH2:29][C:30](=[O:32])[CH3:31]>C(OCC)(=O)C>[OH:32][C:30]1[CH:29]=[CH:28][C:27](/[CH:34]=[CH:11]/[C:10](=[O:12])[CH2:9][C:8]([C:5]2[CH:4]=[CH:3][C:2]([I:1])=[CH:7][CH:6]=2)=[O:13])=[CH:35][C:31]=1[O:16][CH3:15]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 728691-(4-Iodophenyl)ethan-1-oneHCID 817415,5-Dimethylhexane-2,4-dioneHCID 108591511-(4-Iodophenyl)butane-1,3-dione

Product 1

HCID 68815465(E)-5-(4-hydroxy-3-methoxyphenyl)-1-(4-iodophenyl)-pent-4-ene-1,3-dioneYield 31%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

By a similar procedure as described in Example 1 using 1-(4-iodophenyl)-butane-1,3-dione (prepared by reaction of 4-iodoacetophenone with ethyl acetate in the presence of sodium hydride) in place of 5,5-dimethylhexane-2,4-dione, (E)-5-(4-hydroxy-3-methoxyphenyl)-1-(4-iodophenyl)-pent-4-ene-1,3-dione (0.40 g, 0.95 mmol, 31%) was obtained as a yellow solid: mp 139-141° C.; 1H NMR (400 MHz; CDCl3) δ 3.95 (3H, s, OCH3), 5.87 (1H, s, OH), 6.27 (1H, s, H-2), 6.42 (1H, d, J=16.0 Hz, H-4), 6.87 (1H, d, J=8.4 Hz, H-5′), 6.99 (1H, s, H-2′), 7.06 (1H, d, J=8.4 Hz, H-6′), 7.54-7.60 (3H, m, H-5, H-3″, H-5″), 7.41-7.62 (2H, m, H-2″, H-6″), 16.18 (1H, s, OH) ppm; 13C NMR (100 MHz; CDCl3) δ 187.5, 180.8, 148.1, 146.9, 140.9, 138.0, 135.5, 128.9, 127.6, 123.2, 120.9, 115.1, 109.6, 100.0, 97.1, 56.0 ppm.

Sources & evidence

ORD record
ord-9143eac4630d4722b39b8133ea46ccda
Source dataset
uspto-grants-2009_09
Patent number
US07589123B2

Reaction notes

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