Sodium Bicarbonate → HCID 67124168, compound

HRID 1525756Notes

Reaction equation

HRID 1525756 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:24]([F:27])([F:26])[F:25])[O:13][N:12]=[C:11]([C:14]3[CH:19]=[CH:18][C:17]([CH:20]([OH:22])[CH3:21])=[C:16]([CH3:23])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:24]([F:26])([F:25])[F:27])[O:13][N:12]=[C:11]([C:14]3[CH:19]=[CH:18][C:17]([C:20](=[O:22])[CH3:21])=[C:16]([CH3:23])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 67124233HCID 67124233, compound

Product 1

HCID 67124168HCID 67124168, compoundYield 75%

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}-ethanol (i.e. the product of example S.2, Step 1, 160 mg, 0.38 mmol) in CH2Cl2 (10 mL) was added Dess-Martin-Periodinane (243 mg, 0.57 mmol, 1.5 equiv.) in small portions. The mixture was stirred at room temperature over night, then saturated aqueous NaHCO3-solution was added and the mixture was left at room temperature for 1 h. The layers were separated and the organic layer was washed with water, dried over Na2SO4 and evaporated in vacuum to give the title compound (120 mg, 75%), which was used in the next reaction without further purification.

Workup

  1. customThe layers were separated
  2. washthe organic layer was washed with water
  3. dry with materialdried over Na2SO4
  4. customevaporated in vacuum

Sources & evidence

ORD record
ord-61479c15514e43f79cb94d934af35914
Source dataset
uspto-grants-2015_07
Patent number
US09085541B2

Reaction notes

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