Epibromohydrin → HCID 20309567, compound

HRID 596693Notes

Reaction equation

HRID 596693 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]([OH:19])=[C:9]([CH:18]=1)[C:10]([CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[O:11])(=[O:3])[CH3:2].[CH2:20]([CH:22]1[O:24][CH2:23]1)Br>C(C(C)=O)C>[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]([O:19][CH2:20][CH:22]2[O:24][CH2:23]2)=[C:9]([CH:18]=1)[C:10]([CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[O:11])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 18430EpibromohydrinHCID 20309539HCID 20309539, compound

Product 1

HCID 20309567HCID 20309567, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

Methyl 3-(5-acetamido-2-hydroxybenzoyl)propionate (0.75g) anhydrous potassium carbonate (0.39g), epibromohydrin (0.78g) and dry methyl ethyl ketone (20 ml) were stirred and heated under reflux for 16 hours. The cooled reaction mixture was filtered, the filtrate evaporated under reduced pressure and the residual oil purified by elution from a silica column with chloroform/methanol. Methyl 3-[5-acetamido-2-(2,3-epoxypropoxy)benzoyl]propionate was obtained as an oil which solidified, (0.52g, 57%, m.p. 84°-87° C; M+, 321, M 321).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 16 hours
  3. customThe cooled reaction mixture
  4. filtrationwas filtered
  5. customthe filtrate evaporated under reduced pressure
  6. customthe residual oil purified by elution from a silica column with chloroform/methanol

Sources & evidence

ORD record
ord-e85a9f23b1cc4588bbf96612d8ac5f97
Source dataset
uspto-grants-1977_03
Patent number
US04011321

Reaction notes

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