Water → HCID 21270179, compound

HRID 1194464Notes

Reaction equation

HRID 1194464 reaction equation
[CH2:1]1[O:21][C:4]2=[CH:5][C:6]3[O:11][CH:10]=[C:9]([C:12]4[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=4)[C:8](=[O:19])[C:7]=3[CH:20]=[C:3]2[O:2]1.C([O-])([O-])=O.[K+].[K+].Br[CH2:29][CH2:30][O:31][C:32](=[O:36])[CH2:33][CH2:34][CH3:35].O>CN(C)C=O>[CH2:1]1[O:21][C:4]2=[CH:5][C:6]3[O:11][CH:10]=[C:9]([C:12]4[CH:13]=[CH:14][C:15]([O:18][CH:33]([C:32]([O:31][CH2:30][CH3:29])=[O:36])[CH2:34][CH3:35])=[CH:16][CH:17]=4)[C:8](=[O:19])[C:7]=3[CH:20]=[C:3]2[O:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 12636318HCID 12636318, compoundHCID 21270126HCID 21270126, compound

Product 1

HCID 21270179HCID 21270179, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6,7-Methylenedioxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one [cp. Nippon Kagaku Zasshi 85, 793 (1964), Agr. Biol. Chem. (Tokyo) 32, 740 (1968) and Angew. Chem. 93, 129 (1981)] (2.0 g) is dissolved in dimethylformamide (15 ml) and K2CO3 (2.8 g) is added to the solution. While stirring, 2-bromoethylbutyrate (2.7 g) is dropped into the mixture. The content of the reaction flask is refluxed for 30 min. After cooling, water (50 ml) is added and the mixture is extracted with chloroform (3×30 ml), the extract washed with water (3×15 ml) and dried over Na2SO4. Chloroform is removed under reduced pressure and the residue is recrystallized from methanol. The product is dried in vacuo to constant weight to yield 6,7-methylenedioxy-3-[4-(1-ethoxycarbonyl-1-propyloxy)-phenyl]-4H-1-benzopyran-4-one, m.p. 119°-121°.

Workup

  1. temperatureThe content of the reaction flask is refluxed for 30 min
  2. temperatureAfter cooling
  3. extractionthe mixture is extracted with chloroform (3×30 ml)
  4. washthe extract washed with water (3×15 ml)
  5. dry with materialdried over Na2SO4
  6. customChloroform is removed under reduced pressure
  7. customthe residue is recrystallized from methanol
  8. customThe product is dried in vacuo to constant weight

Sources & evidence

ORD record
ord-c90afb2ae182468aba3110d2b5d51f89
Source dataset
uspto-grants-1989_03
Patent number
US04814346

Reaction notes

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