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Potassium Carbonate → HCID 43091431, compound

HRID 2409383
Notes
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Reaction equation

HRID 2409383 reaction equation
Br[CH:2]1[CH2:6][CH2:5][O:4][C:3]1=[O:7].C([O-])([O-])=O.[K+].[K+].C([O:18][C:19](=[O:22])[CH2:20][SH:21])(C)(C)C>CC#N>[O:7]=[C:3]1[CH:2]([S:21][CH2:20][C:19]([OH:22])=[O:18])[CH2:6][CH2:5][O:4]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 954632(3H)-Furanone, 3-bromodihydro-HCID 113555652-Methyl-2-propanyl sulfanylacetate

Product 1

HCID 43091431HCID 43091431, compoundYield 133.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-bromo-dihydro-furan-2-one (16 g, 97.6 mmol) in 300 mL of CH3CN was added K2CO3 (20 g, 146 mmol), followed by mercapto-acetic acid tert-butyl ester (14.5 g, 98 mmol). The reaction mixture was refluxed for 2 hrs and cooled. The mixture was filtered and the filtrate was concentrated. The residue was redissolved in 300 mL of EtOAc and the resulting solution was washed with 1N HCl (100 mL*2). The organic layer was dried over MaSO4, filtered andconcentrated to afford the ter-butyl ester title compound (23 g). 16 g of the ester was dissolved in 250 ml of HCl-MeOH (4M) and stirred at 25° C. for 4 hrs. The reaction mixture was concentrated below 45° C. in vacuum. The residue was purified by column chromatography (EtOAc) to afford 7 g of the title compound.

Workup

  1. temperatureThe reaction mixture was refluxed for 2 hrs
  2. temperaturecooled
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated
  5. dissolutionThe residue was redissolved in 300 mL of EtOAc
  6. washthe resulting solution was washed with 1N HCl (100 mL*2)
  7. customThe organic layer was dried over MaSO4
  8. filtrationfiltered

Sources & evidence

ORD record
ord-19b444efcb1940129d146cb5ec9edd03
Source dataset
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08815873B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes