Sodium Dithionite → HCID 53345776, compound

HRID 1022846Notes

Reaction equation

HRID 1022846 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:27]([F:30])([F:29])[F:28])[O:13][N:12]=[C:11]([C:14]3[CH:19]=[CH:18][C:17]([CH:20]([OH:25])[CH2:21][CH:22]([CH3:24])[CH3:23])=[C:16]([CH3:26])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.C([O-])(O)=O.[Na+].[O-]S(S([O-])=O)=O.[Na+].[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:27]([F:29])([F:28])[F:30])[O:13][N:12]=[C:11]([C:14]3[CH:19]=[CH:18][C:17]([C:20](=[O:25])[CH2:21][CH:22]([CH3:24])[CH3:23])=[C:16]([CH3:26])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 3

HCID 24489Sodium DithioniteHCID 516892Sodium BicarbonateHCID 67447069HCID 67447069, compound2×

Product 1

HCID 53345776HCID 53345776, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-{4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-phenyl}-3-methyl-butan-1-ol (i.e. the product of Step 1, 1.20 g) in CH2Cl2 (50 mL) was added Dess-Martin-Periodinan (CAS [87413-09-0], 1.216 g) in small portions. After 30 min at room temperature, saturated aqueous NaHCO3 and Na2S2O4 solutions were added and the mixture was extracted with CH2Cl2. The organic layer was washed with water, dried (Na2SO4) and concentrated in vacuum. The residue was purified by flash chromatography on silica gel to yield the title compound (1.05 g, 88%).

Workup

  1. extractionthe mixture was extracted with CH2Cl2
  2. washThe organic layer was washed with water
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuum
  5. customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-11f8682b307344d395ddb5f9251db112
Source dataset
uspto-grants-2014_05
Patent number
US08722673B2

Reaction notes

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