Sodium Thiosulfate → HCID 59200992, compound

HRID 1690159Notes

Reaction equation

HRID 1690159 reaction equation
[F:1][C:2]([F:31])([F:30])[C:3]([C:12]1[CH:26]=[CH:25][C:15]([O:16][C:17]2[CH:22]=[CH:21][N:20]=[C:19]([CH2:23][OH:24])[CH:18]=2)=[C:14]([CH2:27][CH2:28][CH3:29])[CH:13]=1)([O:8][CH2:9][O:10][CH3:11])[C:4]([F:7])([F:6])[F:5].I(C1C(C(OO)=O)=CC=CC=1)(=O)=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>CS(C)=O>[F:31][C:2]([F:1])([F:30])[C:3]([C:12]1[CH:26]=[CH:25][C:15]([O:16][C:17]2[CH:22]=[CH:21][N:20]=[C:19]([CH:23]=[O:24])[CH:18]=2)=[C:14]([CH2:27][CH2:28][CH3:29])[CH:13]=1)([O:8][CH2:9][O:10][CH3:11])[C:4]([F:7])([F:6])[F:5]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 59201054HCID 59201054, compoundHCID 86639406HCID 86639406, compound

Product 1

HCID 59200992HCID 59200992, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of (4-(4-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)-2-propylphenoxy)pyridin-2-yl)methanol (110 mg, 446 μmol) in dimethylsulfoxide (3 mL), 2-iodoxyperbenzoic acid (136 mg) was added at room temperature, and the resultant mixture was stirred. After completion of the reaction, the reaction solution was added with a saturated aqueous solution of sodium thiosulfate and a saturated aqueous solution of sodium hydrogen carbonate at room temperature, extracted with ethyl acetate, and then concentrated in vacuo. The obtained residue was purified using silica-gel column chromatography (hexane/ethyl acetate) and the title compound (100 mg, yield 92%) was obtained as a colorless oil.

Workup

  1. customAfter completion of the reaction
  2. extractiona saturated aqueous solution of sodium hydrogen carbonate at room temperature, extracted with ethyl acetate
  3. concentrationconcentrated in vacuo
  4. customThe obtained residue was purified

Sources & evidence

ORD record
ord-8098f47bb7a844abbfecddc660af1881
Source dataset
uspto-grants-2012_04
Patent number
US08153634B2

Reaction notes

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