Epibromohydrin → HCID 20309567, compound

HRID 1763320Notes

Reaction equation

HRID 1763320 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>CC(CC)=O>[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, compoundYield 57.8%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

Methyl 3-(5-acetamido-2-hydroxybenzoyl)propionate (0.75 g, 0.0028 mole) anhydrous potassium carbonate (0.39 g, 0.0028 mole), epibromohydrin (0.78 g, 0.00565 mole) and dry ethyl methyl ketone (20 ml) were stirred and heated under reflux for 16 hours. The cooled mixture was filtered and evaporated under reduced pressure to an oil which was purified by elution from a silica column with chloroform-methanol to give methyl 3-[5-acetamido-2-(2,3-epoxypropoxy)-benzoyl]propionate (0.52 g, 57%, m.p. 84°-87°). (Found: M+, 321, C16H19NO6 requires M, 321).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 16 hours
  3. filtrationThe cooled mixture was filtered
  4. customevaporated under reduced pressure to an oil which
  5. customwas purified by elution from a silica column with chloroform-methanol

Sources & evidence

ORD record
ord-1143662e3892460885bfc3159540486a
Source dataset
uspto-grants-1978_09
Patent number
US04111936

Reaction notes

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