Sodium Sulfite → HCID 86718612, compound

HRID 1480646Notes

Reaction equation

HRID 1480646 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:18]2[CH:19]=[N:20][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:22][CH:23]=2)[C:8]([O:14][CH2:15][O:16][CH3:17])=[C:9]([CH:11]([OH:13])[CH3:12])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)(O)[O-].[Na+].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl.[Cl-].[Na+].O.O>[C:1]([C:5]1[CH:6]=[C:7]([C:18]2[CH:19]=[N:20][C:21]([C:24]([F:27])([F:25])[F:26])=[CH:22][CH:23]=2)[C:8]([O:14][CH2:15][O:16][CH3:17])=[C:9]([C:11](=[O:13])[CH3:12])[CH:10]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

8

Reactant 4

HCID 24437Sodium SulfiteHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 86718611HCID 86718611, compound

Product 1

HCID 86718612HCID 86718612, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 1-(5-(tert-butyl)-2-(methoxymethoxy)-3-(6-(trifluoromethyl)pyridin-3-yl)phenyl)ethan-1-ol (529 mg, 1.38 mmol) and sodium bicarbonate (1.16 g, 13.8 mmol) in methylene chloride (40 mL) was added Dess Martin periodinane (3.00 g, 6.90 mmol) and the reaction stirred for 1 hour. The reaction mixture was poured onto a 1:1 mixture of saturated aqueous sodium sulfite solution (50 mL) and water (50 mL). The resulting mixture was extracted with ethyl acetate (150 mL). The organic phase was washed with 1 N aqueous sodium hydroxide solution (50 mL), and water (50 mL), an emulsion formed and saturated brine (100 mL) was added to separate layers. The organic phase was dried (MgSO4), filtered and the solvent removed under reduced pressure. The residue was purified using flash chromatography on silica eluting with a solvent gradient of 0 to 100% ethyl acetate in hexanes to give 1-(5-(tert-butyl)-2-(methoxymethoxy)-3-(6-(trifluoromethyl)pyridin-3-yl)phenyl)ethan-1-one (526 mg, 100% yield) as a white solid.

Workup

  1. extractionThe resulting mixture was extracted with ethyl acetate (150 mL)
  2. washThe organic phase was washed with 1 N aqueous sodium hydroxide solution (50 mL), and water (50 mL)
  3. customan emulsion formed
  4. customto separate layers
  5. dry with materialThe organic phase was dried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent removed under reduced pressure
  8. customThe residue was purified

Sources & evidence

ORD record
ord-f1b0a25c7bcb42a1ac4a7ff1328c24f1
Source dataset
uspto-grants-2016_08
Patent number
US09409893B2

Reaction notes

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