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Potassium Carbonate → Methyl 4-(3-(4-acetyl-3-hydroxy-2-propylphenoxy)propylthio)-gamma-oxo-beta-methyl-2-bromobenzenebutanoate

HRID 846245
Notes
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Reaction equation

HRID 846245 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([SH:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:17])[CH:10]([CH3:16])[CH2:11][C:12]([O:14][CH3:15])=[O:13].[C:18]([C:21]1[CH:31]=[CH:30][C:24]([O:25][CH2:26][CH2:27][CH2:28]Br)=[C:23]([CH2:32][CH2:33][CH3:34])[C:22]=1[OH:35])(=[O:20])[CH3:19].C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C.C(OCC)(=O)C>[C:18]([C:21]1[CH:31]=[CH:30][C:24]([O:25][CH2:26][CH2:27][CH2:28][S:8][C:6]2[CH:5]=[CH:4][C:3]([C:9](=[O:17])[CH:10]([CH3:16])[CH2:11][C:12]([O:14][CH3:15])=[O:13])=[C:2]([Br:1])[CH:7]=2)=[C:23]([CH2:32][CH2:33][CH3:34])[C:22]=1[OH:35])(=[O:20])[CH3:19]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27752211-[4-(3-Bromopropoxy)-2-hydroxy-3-propylphenyl]ethanoneHCID 19884853Methyl 2-bromo-4-mercapto-gamma-oxo-beta-methylbenzenebutanoate

Product 1

HCID 19884798Methyl 4-(3-(4-acetyl-3-hydroxy-2-propylphenoxy)propylthio)-gamma-oxo-beta-methyl-2-bromobenzenebutanoate

Reagents, catalysts & solvents 2

HCID 6569
Methyl Ethyl Ketone
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the thiol from step C (2.9 g) and 3-(4-acetyl-3-hydroxy-2-propylphenoxy)propylbromide (3.74 g) in methyl ethyl ketone (25 c.c.) was added potassium carbonate (3.78 g, milled) and the suspension was refluxed for 21/2 hours, then stirred at R.T. for 12 hours. The mixture was diluted with ethyl acetate (25 c.c.) and the insolubles filtered off. The filtrate was concentrated to dryness in vacuo and the residue purified on silica gel to yield the title compound as an oil.

Workup

  1. temperaturethe suspension was refluxed for 21/2 hours
  2. filtrationthe insolubles filtered off
  3. concentrationThe filtrate was concentrated to dryness in vacuo
  4. customthe residue purified on silica gel

Sources & evidence

ORD record
ord-16814c7e21d94d219db243fcf1e78f37
Source dataset
uspto-grants-1992_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05135940

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes