p-Toluenesulfonic acid → HCID 86718613, compound

HRID 1480647Notes

Reaction equation

HRID 1480647 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]COC)=[C:9]([C:11](=[O:13])[CH3:12])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[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]([OH:14])=[C:9]([C:11](=[O:13])[CH3:12])[CH:10]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 86718612HCID 86718612, compound

Product 1

HCID 86718613HCID 86718613, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 1-(5-(tert-butyl)-2-(methoxymethoxy)-3-(6-(trifluoromethyl)pyridin-3-yl)phenyl)ethan-1-one (440 mg, 1.15 mmol) in methanol (5 mL) was added para-toluenesulfonic acid (330 mg, 1.72 mmol) and the reaction mixture heated to 40° C. After 30 minutes the reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution. The organic phase was separated, dried (Na2SO4), filtered and purified by flash chromatography on silica eluting with 0-100% ethyl acetate in hexanes to yield 1-(5-(tert-butyl)-2-hydroxy-3-(6-(trifluoromethyl)pyridin-3-yl)phenyl)ethan-1-one (338 mg, 87%) as a cream colored solid.

Workup

  1. customAfter 30 minutes the reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution
  2. customThe organic phase was separated
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. custompurified by flash chromatography on silica eluting with 0-100% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-2751f37cd32240c3b82321d6c807083c
Source dataset
uspto-grants-2016_08
Patent number
US09409893B2

Reaction notes

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