Sodium Thiosulfate → HCID 68673705, compound

HRID 1927681Notes

Reaction equation

HRID 1927681 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[Br:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][C:32]([NH:34][CH2:35][CH:36]([OH:43])[CH2:37][C:38]([CH3:42])([CH3:41])[CH2:39][CH3:40])=[O:33])=[CH:26][CH:25]=1.C([O-])(O)=O.[Na+].[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)Cl>[Br:23][C:24]1[CH:25]=[CH:26][C:27]([CH2:30][CH2:31][C:32]([NH:34][CH2:35][C:36](=[O:43])[CH2:37][C:38]([CH3:42])([CH3:41])[CH2:39][CH3:40])=[O:33])=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 68674059HCID 68674059, compound

Product 1

HCID 68673705HCID 68673705, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin reagent (38.8 g, 91.5 mmol) was added to a solution of 3-(4-bromophenyl)-N-(2-hydroxy-4,4-dimethylhexyl)propanamide (29.6 g, 83.2 mmol) in CH2Cl2 (400 mL) at rt. After stirring for 1 h, a solution of saturated aqueous NaHCO3 and saturated aqueous Na2S2O3 (1:1) was added and the solution was stirred until it became clear. The solution was extracted with ethyl acetate. The organic layer was dried (MgSO4), filtered, and concentrated in vacuo to give a residue. The residue was purified by flash column chromatography on silica gel eluting with 0-50% EtOAc/hexanes to provide 3-(4-bromophenyl)-N-(4,4-dimethyl-2-oxohexyl)propanamide.

Workup

  1. stirringthe solution was stirred until it
  2. extractionThe solution was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give a residue
  7. customThe residue was purified by flash column chromatography on silica gel eluting with 0-50% EtOAc/hexanes

Sources & evidence

ORD record
ord-ffc9bc14a5ee48c7b45e7900accf9f11
Source dataset
uspto-grants-2012_05
Patent number
US08183275B2

Reaction notes

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