Isobutyryl chloride → HCID 20522535, compound

HRID 223129Notes

Reaction equation

HRID 223129 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[C:8]2[C:3]=1[C:4](=[O:31])[C:5]([O:29][CH3:30])=[C:6]([C:14]1[CH:19]=[CH:18][C:17]([O:20][C:21](=[O:26])[C:22]([CH3:25])([CH3:24])[CH3:23])=[C:16]([O:27][CH3:28])[CH:15]=1)[O:7]2.[C:32](Cl)(=[O:36])[CH:33]([CH3:35])[CH3:34]>N1C=CC=CC=1>[C:32]([O:1][C:2]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[C:8]2[C:3]=1[C:4](=[O:31])[C:5]([O:29][CH3:30])=[C:6]([C:14]1[CH:19]=[CH:18][C:17]([O:20][C:21](=[O:26])[C:22]([CH3:25])([CH3:23])[CH3:24])=[C:16]([O:27][CH3:28])[CH:15]=1)[O:7]2)(=[O:36])[CH:33]([CH3:35])[CH3:34]

Participants

4

Reactant 2

HCID 62325Isobutyryl chlorideHCID 20522556HCID 20522556, compound

Product 1

HCID 20522535HCID 20522535, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution containing 0.2 g of 5-hydroxy-3,3',7-trimethoxy-4'-(pivaloyloxy)-flavone in 3 ml of pyridine was added 0.05 ml of isobutyryl chloride and the mixture was stirred at room temperature for 3 hours. After removal of the solvent by evaporation under reduced pressure, the resulting oily residue was dissolved in 5 ml of a mixed solvent of ethanol and hexane (1:1, v/v). The solution was allowed to stand in a refrigerator overnight, during which time crystallisation occurred. The crystals were collected by filtration, washed with hexane and dried. There were obtained 200 mg of 5-(isobutyryloxy)-3,3',7-trimethoxy-4'-(pivaloyloxy)-flavone as colourless needles: m.p. 151°-152° C.

Workup

  1. customAfter removal of the solvent
  2. customby evaporation under reduced pressure
  3. dissolutionthe resulting oily residue was dissolved in 5 ml of a mixed solvent of ethanol and hexane (1:1
  4. customto stand in a refrigerator overnight, during which time crystallisation
  5. filtrationThe crystals were collected by filtration
  6. washwashed with hexane
  7. customdried

Sources & evidence

ORD record
ord-054bdf30ee104d03acc93afbd8680ad1
Source dataset
uspto-grants-1982_10
Patent number
US04352792

Reaction notes

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