Water → HCID 66816624, compound

HRID 1754975Notes

Reaction equation

HRID 1754975 reaction equation
CC(C)([O-])C.[K+].Br[CH2:8][C:9]([N:11]([C:15]1[CH:20]=[C:19]([CH3:21])[C:18]([Br:22])=[C:17]([CH3:23])[CH:16]=1)[CH2:12][CH2:13][OH:14])=[O:10].O>CC(O)(C)C>[Br:22][C:18]1[C:19]([CH3:21])=[CH:20][C:15]([N:11]2[CH2:12][CH2:13][O:14][CH2:8][C:9]2=[O:10])=[CH:16][C:17]=1[CH3:23]

Participants

5

Reactant 3

HCID 962WaterHCID 23665647Potassium tert-butoxideHCID 66817502HCID 66817502, compound

Product 1

HCID 66816624HCID 66816624, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

Potassium t-butoxide (53 mg, 0.44 mmol) was added to a solution of 2-bromo-N-(4-bromo-3,5-dimethyl-phenyl)-N-(2-hydroxy-ethyl)-acetamide (147 mg, 0.40 mmol) in t-BuOH (2 ml), and the mixture was heated under reflux overnight. The reaction solution was cooled to room temperature and water was then added, followed by extraction with ethyl acetate. The organic phase was washed with saturated brine and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give 4-(4-bromo-3,5-dimethyl-phenyl)-morpholin-3-one (100%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux overnight
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic phase was washed with saturated brine
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-0662a0b5cfa74b43b7968aae938918a3
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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