3-Methoxyphenol → HCID 10136636, compound

HRID 1768415Notes

Reaction equation

HRID 1768415 reaction equation
[CH3:1][O:2][C:3]1C=C(O)[CH:6]=[CH:7][CH:8]=1.[H-].[Na+].[CH2:12]([O:14][C:15](=[O:31])[C:16]([C:29]#[N:30])=[CH:17][C:18]1[CH:23]=[C:22]([O:24][CH3:25])[C:21]([O:26][CH3:27])=[C:20]([Br:28])[CH:19]=1)[CH3:13]>C1(C)C=CC=CC=1>[C:29]([C:16]1[C:15](=[O:31])[O:14][C:12]2[C:6]([C:17]=1[C:18]1[CH:23]=[C:22]([O:24][CH3:25])[C:21]([O:26][CH3:27])=[C:20]([Br:28])[CH:19]=1)=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:13]=2)#[N:30]

Participants

5

Reactant 3

HCID 90073-MethoxyphenolHCID 24758Sodium hydrideHCID 69507278HCID 69507278, compound

Product 1

HCID 10136636HCID 10136636, compoundYield 1.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 5-bromoveratraldehyde (1.0 g, 4.1 mmol) and ethyl cyanoacetate (0.45 mL, 4.1 mmol) in ethanol (4 mL) was added piperidine (0.4 mL, 4.1 mmol). The mixture was stirred at room temperature for 0.5 h and precipitate was collected by filtration to yield the product (1.16 g) 3-(3-bromo-4,5-dimethoxy-phenyl)-2-cyano-acrylic acid ethyl ester as a solid. To a solution of 3-methoxyphenol (0.11 mL, 1 mmol) in toluene (10 mL) was added sodium hydride (60 mg, 1.5 mmol, 60%) and the mixture was stirred at room temperature for 0.5 h. To the mixture was added 3-(3-bromo-4,5-dimethoxy-phenyl)-2-cyano-acrylic acid ethyl ester (340 mg, 1 mmol) as a solid, then the mixture was refluxed for 2 h. The solvent was evaporated and the residue was purified by chromatography on silica gel with ethyl acetate and hexane (1:2) as eluant, yielding 7 mg (1.7%) of the title compound. 1H NMR (CDCl3): 7.34 (d, J=9.6, 1H), 7.21 (d, J=1.8, 1H), 6.98 (d, J=1.8, 1H), 6.91-6.90 (m, 2H), 3.98 (s, 3H), 3.94 (s, 3H), 3.93 (s, 3H).

Workup

  1. temperaturethe mixture was refluxed for 2 h
  2. customThe solvent was evaporated
  3. customthe residue was purified by chromatography on silica gel with ethyl acetate and hexane (1:2) as eluant

Sources & evidence

ORD record
ord-7d569ce531fe4a0ba91eae6c49825327
Source dataset
uspto-grants-2007_06
Patent number
US07235674B2

Reaction notes

Loading…