Water → HCID 23469768, compound

HRID 128466Notes

Reaction equation

HRID 128466 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[C:10]([Br:15])[CH:9]=1)=[O:7].[OH-].[K+].Br[C:19]([CH3:26])([CH3:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21].O>CS(C)=O>[Br:15][C:10]1[CH:9]=[C:8]([C:6](=[O:7])[C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)[CH:13]=[CH:12][C:11]=1[O:14][C:19]([CH3:26])([CH3:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21]

Participants

6

Reactant 4

HCID 962WaterHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 14797Potassium HydroxideHCID 23469770HCID 23469770, compound

Product 1

HCID 23469768HCID 23469768, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-thienyl-(3-bromo-4-hydroxy-phenyl)ketone (14.5 g; M.p.=185° C.) in dimethylsulfoxide (50 ml) is added potassium hydroxide (2.8 g) and the mixture is heated to 50° C. for 30 minutes, after which ethyl α-bromoisobutyrate (9.75 g) is added thereto at room temperature. After a period of time of 3 hours, the solution is poured into water (100 ml) and the aqueous phase is extracted with ethyl ether. The organic phase is washed with an aqueous sodium hydroxide solution, and then with water, and the solvent is evaporated off after drying over sodium sulfate. The final product is recrystallized from petroleum ether (7 g; M.p.=80° C.).

Workup

  1. customat room temperature
  2. extractionthe aqueous phase is extracted with ethyl ether
  3. washThe organic phase is washed with an aqueous sodium hydroxide solution
  4. customwith water, and the solvent is evaporated off
  5. dry with materialafter drying over sodium sulfate
  6. customThe final product is recrystallized from petroleum ether (7 g; M.p.=80° C.)

Sources & evidence

ORD record
ord-2ef16ef45a154e72adb4834a0217689d
Source dataset
uspto-grants-1981_03
Patent number
US04259509

Reaction notes

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