2,5-Dimethoxyphenyl vinyl ketone → HCID 19021027, compound

HRID 1109615Notes

Reaction equation

HRID 1109615 reaction equation
[CH:1]([C:3]([C:5]1[CH:10]=[C:9]([O:11]C)[CH:8]=[CH:7][C:6]=1[O:13]C)=[O:4])=[CH2:2]>C(#N)C.O>[C:3]([C:5]1[C:6](=[O:13])[CH:7]=[CH:8][C:9](=[O:11])[CH:10]=1)(=[O:4])[CH:1]=[CH2:2]

Participants

4

Reactant 1

HCID 127134602,5-Dimethoxyphenyl vinyl ketone

Product 1

HCID 19021027HCID 19021027, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 2,5-dimethoxyphenyl vinyl ketone (2.5 g, 0.013 mole) in 25 ml of acetonitrile at 0° C. was added dropwise over 3 minutes an aqueous solution of (NH4)2Ce(NO2)6 (17.9 g, 0.033 mole) in 30 ml of water. After the addition, the dark brown mixture turned to yellowish-brown within 5 minutes. At that point, the mixture was poured into water and extracted with methylene chloride. The methylene chloride portion was washed twice with water and then with brine. After drying (MgSO4), the solvent was removed to give a brown oil, which was purified by column chromatography on silica gel, using diethyl ether/hexane (1/1) as eluant. The product was obtained as a reddish/orange, semi-solid residue; 0.8 g; IR (neat) 1670 cm-1 ; NMR (CDCl3) δ5.95 (d, 1H); 6.5-7.2 (m, 5H).

Workup

  1. additionAfter the addition
  2. customyellowish-brown within 5 minutes
  3. extractionextracted with methylene chloride
  4. washThe methylene chloride portion was washed twice with water
  5. dry with materialAfter drying (MgSO4)
  6. customthe solvent was removed
  7. customto give a brown oil, which
  8. customwas purified by column chromatography on silica gel
  9. customThe product was obtained as a reddish/orange, semi-solid residue

Sources & evidence

ORD record
ord-4bddae8f40d44cdd9a24687fa71d661f
Source dataset
uspto-grants-1994_06
Patent number
US05321141

Reaction notes

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