Trimethylsilyl triflate → HCID 86675228, compound

HRID 1504726Notes

Reaction equation

HRID 1504726 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([C:12](=[O:14])[CH3:13])=[CH:8][CH:7]=2)[CH:5]=[N:4][CH:3]=[N:2]1.FC(F)(F)S(O[Si:21]([CH3:24])([CH3:23])[CH3:22])(=O)=O>C(Cl)Cl>[CH3:22][Si:21]([CH3:24])([CH3:23])[O:14][C:12]([C:9]1[CH:8]=[CH:7][C:6]([N:1]2[CH:5]=[N:4][CH:3]=[N:2]2)=[CH:11][CH:10]=1)=[CH2:13]

Participants

4

Reactant 2

HCID 65367Trimethylsilyl triflateHCID 25603171-[4-(1H-1,2,4-Triazol-1-yl)phenyl]ethan-1-one

Product 1

HCID 86675228HCID 86675228, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-(4-(1H-1,2,4-triazol-1-yl)phenyl)ethanone (4.5 g, 24.0 mmol) in CH2Cl2 at 0° C., were added TEA (3.7 g, 36.1 mmol) and trimethylsilyl trifluoromethanesulfonate (8 g, 36 mmol) and the resultant reaction mixture was stirred for 1 h. The reaction mixture was quenched with a mixture of sat aq sodium bicarbonate solution and ether. The ether layer and was separated, washed with brine, dried over Na2SO4 and concentrated under reduced pressure to afford the title compound (5.5 g) which was taken directly to next step.

Workup

  1. customthe resultant reaction mixture
  2. customThe reaction mixture was quenched with a mixture of sat aq sodium bicarbonate solution and ether
  3. customThe ether layer and was separated
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-523e3f76f4754d9281e262d1e92cc53e
Source dataset
uspto-grants-2015_12
Patent number
US09215870B2

Reaction notes

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