Water → HCID 21270214, compound

HRID 1194463Notes

Reaction equation

HRID 1194463 reaction equation
[OH:1][C:2]1[CH:22]=[CH:21][C:5]2[C:6](=[O:20])[C:7]([C:10]3[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=3)=[CH:8][O:9][C:4]=2[C:3]=1[CH3:23].C([O-])([O-])=O.[K+].[K+].[CH2:30]([CH:32]1[O:34][CH2:33]1)Br.O>CN(C)C=O>[O:34]1[CH2:33][CH:32]1[CH2:30][O:1][C:2]1[CH:22]=[CH:21][C:5]2[C:6](=[O:20])[C:7]([C:10]3[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=3)=[CH:8][O:9][C:4]=2[C:3]=1[CH3:23]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 18430EpibromohydrinHCID 21270165HCID 21270165, compound

Product 1

HCID 21270214HCID 21270214, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7-Hydroxy-8-methyl-3-(3,4-dimethoxyphenyl)-4H-1-benzoyran-4-one [see example 12] (3.12 g) is dissolved in dimethylformamide (15 ml) and K2CO3 (3.5 g) is added to the solution. While stirring, epibromhydrine (2.47 g) is dropped into the mixture. After heating for 5 h at 60°, the content of the reaction flask is poured into water (500 ml) and the precipitated product is filtered off and recrystallized from ethanol. The product is dried in vacuo to constant weight to yield 7-(2,3-epoxypropoxy)-8-methyl-3-(3,4-dimethoxyphenyl)-4H-1-benzopyran-4-one, m.p. 214°.

Workup

  1. temperatureAfter heating for 5 h at 60°
  2. filtrationthe precipitated product is filtered off
  3. customrecrystallized from ethanol
  4. customThe product is dried in vacuo to constant weight

Sources & evidence

ORD record
ord-bb5ca7f822ed429d908c608c418acf95
Source dataset
uspto-grants-1989_03
Patent number
US04814346

Reaction notes

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