Pyridine → HCID 86636040, compound

HRID 1405932Notes

Reaction equation

HRID 1405932 reaction equation
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].[C:16]1([C:22]([C:25]2[CH:30]=[CH:29][C:28](O)=[CH:27][CH:26]=2)([CH3:24])[CH3:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.N1C=CC=CC=1>CC#N>[F:1][C:2]([F:15])([F:14])[S:3]([O:6][C:28]1[CH:29]=[CH:30][C:25]([C:22]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([CH3:24])[CH3:23])=[CH:26][CH:27]=1)(=[O:5])=[O:4]

Participants

5

Reactant 3

HCID 1049PyridineHCID 117424-CumylphenolHCID 67749Trifluoromethanesulfonic anhydride

Product 1

HCID 86636040HCID 86636040, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Trifluoromethanesulfonic anhydride (1.99 mL) was added dropwise to a solution of 4-(2-phenylpropan-2-yl)phenol (1.68 g) and pyridine (1.277 mL) in MeCN (10 mL) at 0° C. The mixture was stirred at room temperature for 2 days. The mixture was quenched with 0.1 N HCl aq. at 0° C. and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over anhydrous magnesium sulfate, filtered through silica-Celite pad (eluted with EtOAc) and concentrated in vacuo to give 4-(2-phenylpropan-2-yl)phenyl trifluoromethanesulfonate (2.65 g) as a yellow oil.

Workup

  1. customThe mixture was quenched with 0.1 N HCl aq. at 0° C.
  2. extractionextracted with EtOAc
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered through silica-Celite pad (eluted with EtOAc)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-337bf286b21c40e5ae6b804c9c888a28
Source dataset
uspto-grants-2014_12
Patent number
US08916551B2

Reaction notes

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