Chlorotrimethylsilane → HCID 14978355, compound

HRID 875240Notes

Reaction equation

HRID 875240 reaction equation
[CH3:1][N:2]1[CH:6]=[N:5][N:4]=[C:3]1[C:7]#N.C[Si](Cl)(C)C.[C:14]1([Mg]Br)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C1C[O:25]CC1>>[CH3:1][N:2]1[CH:6]=[N:5][N:4]=[C:3]1[C:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:25]

Participants

5

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 8028TetrahydrofuranHCID 66886754HCID 66886754, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 14978355HCID 14978355, compoundYield 48%

Conditions

Temperature
-40 °C

Procedure

To a solution of 4-methyl-4H-1,2,4-triazole-3-carbonitrile (70%, 4.27 g, 27.64 mmol, 1 eq.) in 200 ml of THF cooled to −40° C. was added TMSCl (6.0 g, 55.29 mmol, 2.0 eq.) followed by phenylmagnesium bromide (2.8 M, 14.81 ml, 41.47 mmol, 1.4 eq.). The reaction was stirred at −40° C. for 1 h and quenched with 1N HCl. EtOAc was added and the layers separated. The aqueous layer was extracted with EtOAc and the organics combined, dried over MgSO4 and concentrated. The residue was triturated in EtOAc and the solid removed by filtration. The crude was purified by chromatography on silica gel to give (4-methyl-4H-1,2,4-triazol-3-yl)(phenyl)methanone (2.45 g, 48% yield) as a yellow solid.

Workup

  1. customquenched with 1N HCl
  2. additionEtOAc was added
  3. customthe layers separated
  4. extractionThe aqueous layer was extracted with EtOAc
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was triturated in EtOAc
  8. customthe solid removed by filtration
  9. customThe crude was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-321fe2c11c334e2187eda1d6539417fe
Source dataset
uspto-grants-2015_03
Patent number
US08981111B2

Reaction notes

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