2-[4-Hydroxyphenyl]-3-(3,5-dimethoxyphenyl)acrylic acid methyl ester → HCID 21051258, compound

HRID 2238248Notes

Reaction equation

HRID 2238248 reaction equation
[CH3:1][O:2][C:3](=[O:23])[C:4]([C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)=[CH:5][C:6]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[C:8]([O:14][CH3:15])[CH:7]=1>C(O)C>[CH3:1][O:2][C:3](=[O:23])[CH:4]([C:16]1[CH:17]=[CH:18][C:19]([OH:22])=[CH:20][CH:21]=1)[CH2:5][C:6]1[CH:7]=[C:8]([O:14][CH3:15])[CH:9]=[C:10]([O:12][CH3:13])[CH:11]=1

Participants

3

Reactant 1

HCID 687765982-[4-Hydroxyphenyl]-3-(3,5-dimethoxyphenyl)acrylic acid methyl ester

Product 1

HCID 21051258HCID 21051258, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 8 (6.28 g, 20.0 mmol) in ethanol (200 mL) palladium on carbon (10%, wet, 0.63 g) was added and stirred under H2 at atmospheric pressure at room temperature for 18 h. Catalyst was filtered through a bed of Celite® and solvent was evaporated under reduced pressure to yield 15 as white solid (6.32 g, 100%): mp 63-65° C.; 1HNMR (400 MHz, DMSO-d6): δ 7.15 (d, J=8.7 Hz, 2H), 6.74 (d, J=8.7 Hz, 2H), 6.29 (t, J=2.4 Hz, 1H), 6.25 (d, J=2.4 Hz, 2H), 3.78 (t, J=8.7 Hz, 1H), 3.72 (s, 6H), 3.62 (s, 3H), 3.31 (dd, J=13.5 and 8.4 Hz, 1H), 2.93 (dd, J=13.5 and 6.9 Hz, 1H); MS (EI) m/z 317[M]+; Anal. (C18H20O5) C, H.

Workup

  1. additionwas added
  2. filtrationCatalyst was filtered through a bed of Celite® and solvent
  3. customwas evaporated under reduced pressure

Sources & evidence

ORD record
ord-8897200e92e24b8f9997b71843076aaa
Source dataset
uspto-grants-2010_05
Patent number
US07718682B2

Reaction notes

Loading…