Sodium Thiosulfate → HCID 58452337, compound

HRID 70528Notes

Reaction equation

HRID 70528 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=[O:3].[C:23]([C:27]1[CH:32]=[CH:31][C:30](/[C:33](/[C:37]2[CH:42]=[CH:41][C:40]([Cl:43])=[C:39]([O:44][CH3:45])[N:38]=2)=[CH:34]\[CH2:35][OH:36])=[CH:29][CH:28]=1)([CH3:26])([CH3:25])[CH3:24].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)(Cl)Cl>[C:23]([C:27]1[CH:32]=[CH:31][C:30](/[C:33](/[C:37]2[CH:42]=[CH:41][C:40]([Cl:43])=[C:39]([O:44][CH3:45])[N:38]=2)=[CH:34]\[C:35]([OH:3])=[O:36])=[CH:29][CH:28]=1)([CH3:26])([CH3:24])[CH3:25]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 58452849(2E)-3-(4-tert-Butylphenyl)-3-(5-chloro-6-methoxypyridin-2-yl)prop-2-en-1-ol

Product 1

HCID 58452337HCID 58452337, compoundYield 69.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Dess-Martin reagent (770 mg) was added to a solution of (2E)-3-(4-tert-butylphenyl)-3-(5-chloro-6-methoxypyridin-2-yl)prop-2-en-1-ol (601 mg) in chloroform (20 mL), and the mixture was stirred at room temperature for 30 minutes. A 10% sodium thiosulfate solution was added to the reaction solution, followed by extraction with chloroform. The organic layer was washed with brine and dried over sodium sulfate. After filtration, the solvent was evaporated under reduced pressure. Sodium dihydrogenphosphate (1.0 g) and chlorous acid (1.6 g) were added to a solution of the resulting residue and 2-methyl-2-butene (2.3 g) in tert-butanol (15 mL)-water (5 mL), and the mixture was stirred at room temperature for one hour. The reaction solution was ice-cooled and then adjusted to a pH of less than 2 with 1 M hydrochloric acid, followed by extraction with chloroform. The organic layer was washed with brine and dried over sodium sulfate. After filtration, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=9:1). Thereafter, the resulting solid was washed with hexane and then dried to give the title compound as a colorless powder (434 mg, 69%).

Workup

  1. extractionfollowed by extraction with chloroform
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationAfter filtration
  5. customthe solvent was evaporated under reduced pressure
  6. additionSodium dihydrogenphosphate (1.0 g) and chlorous acid (1.6 g) were added to a solution of the resulting residue and 2-methyl-2-butene (2.3 g) in tert-butanol (15 mL)-water (5 mL)
  7. stirringthe mixture was stirred at room temperature for one hour
  8. temperaturecooled
  9. extractionfollowed by extraction with chloroform
  10. washThe organic layer was washed with brine
  11. dry with materialdried over sodium sulfate
  12. filtrationAfter filtration
  13. customthe solvent was evaporated under reduced pressure
  14. customThe residue was purified by silica gel column chromatography (chloroform:methanol=9:1)
  15. washThereafter, the resulting solid was washed with hexane
  16. customdried

Sources & evidence

ORD record
ord-bde324b1594e4ceab785a79751fc0bc9
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

Loading…