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Sodium Acetate → Ethyl [1-(4-chlorobenzyl)-3-t-butylthio-5-allyloxyindol-2-yl]carboxylate

HRID 1590104
Notes
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Reaction equation

HRID 1590104 reaction equation
[C:1]([S:5][CH2:6][C:7](=O)[C:8]([O:10][CH2:11][CH3:12])=[O:9])([CH3:4])([CH3:3])[CH3:2].Cl.[Cl:15][C:16]1[CH:34]=[CH:33][C:19]([CH2:20][N:21]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH:31]=[CH2:32])=[CH:25][CH:24]=2)N)=[CH:18][CH:17]=1.CC([O-])=O.[Na+]>C1(C)C=CC=CC=1.CC(O)=O>[Cl:15][C:16]1[CH:34]=[CH:33][C:19]([CH2:20][N:21]2[C:23]3[C:24](=[CH:25][C:26]([O:29][CH2:30][CH:31]=[CH2:32])=[CH:27][CH:28]=3)[C:6]([S:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[C:7]2[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:18][CH:17]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 14919330Ethyl 3-(tert-butylsulfanyl)-2-oxopropanoateHCID 19023706HCID 19023706, compound

Product 1

HCID 21746950Ethyl [1-(4-chlorobenzyl)-3-t-butylthio-5-allyloxyindol-2-yl]carboxylate

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent
HCID 1140
Toluene
Solvent

Procedure

A solution of 18.6 g ethyl 3-t-butylthio-2-oxopropanoate, 26.3 g 1-(4-chlorobenzyl)-1-(4-allyloxyphenyl)hydrazine hydrochloride and 15 g NaOAc in 300 mL toluene and 150 mL HOAc was stirred at room temperature under nitrogen for 16 hours then at 70° C. for 2 hour. The mixture was cooled, poured onto H2O, extracted (3×) EtOAc and the organic layers then washed successively with sat. NaHCO3 and brine. After drying over MgSO4 the solution was filtered, evaporated and the residue chromatographed (silica gel; hexane/EtOAc 4:1) to afford the title compound.

Workup

  1. temperatureThe mixture was cooled
  2. additionpoured onto H2O
  3. extractionextracted (3×) EtOAc
  4. washthe organic layers then washed successively with sat. NaHCO3 and brine
  5. dry with materialAfter drying over MgSO4 the solution
  6. filtrationwas filtered
  7. customevaporated
  8. customthe residue chromatographed (silica gel; hexane/EtOAc 4:1)

Sources & evidence

ORD record
ord-1cbcbf23cb1e4bca98ec16b25e53c7a4
Source dataset
uspto-grants-1993_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05202321

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes