Triethylsilane → HCID 19349418, compound

HRID 2107779Notes

Reaction equation

HRID 2107779 reaction equation
O[C:2]([C:5]1[CH:6]=[C:7]([C:17]([CH3:21])([CH3:20])[C:18]#[N:19])[CH:8]=[C:9]([CH2:11][N:12]2[CH:16]=[N:15][CH:14]=[N:13]2)[CH:10]=1)([CH3:4])[CH3:3].C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[CH:2]([C:5]1[CH:6]=[C:7]([C:17]([CH3:21])([CH3:20])[C:18]#[N:19])[CH:8]=[C:9]([CH2:11][N:12]2[CH:16]=[N:15][CH:14]=[N:13]2)[CH:10]=1)([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 19349415HCID 19349415, compound

Product 1

HCID 19349418HCID 19349418, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 2-[3-(1-hydroxy-1-methylethyl)-5-(1H-1,2,4-triazol-1-ylmethyl)phenyl]-2-methylpropiononitrile (0.06 g) in trifluoroacetic acid (1 ml) was treated with triethylsilane (50 mg) and the solution kept at room temperature for 18 h and then evaporated to dryness under reduced pressure. The residue was treated with aqueous sodium hydrogen carbonate solution and the mixture was extracted twice with ethyl acetate. The combined extracts were dried and evaporated to dryness under reduced pressure, and the residue was purified by flash chromatography, using ethyl acetate as eluant, to give 2-[3-isopropyl-5-(1H-1,2,4-triazol-1-ylmethyl)phenyl]-2-methylpropiononitrile. Nmr in deuteriochloroform: δ 8.1 (1H, s), 8.0 (1H, s), 7.32 (1H, m), 7.18 (1H, m), 7.05 (1H, m), 5.35 (2H, s), 2.92 (1H, m), 1.7 (6H, s), 1.24 (6H, d).

Workup

  1. customevaporated to dryness under reduced pressure
  2. additionThe residue was treated with aqueous sodium hydrogen carbonate solution
  3. extractionthe mixture was extracted twice with ethyl acetate
  4. customThe combined extracts were dried
  5. customevaporated to dryness under reduced pressure
  6. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-018cad0563af409dbd3f002a31080df2
Source dataset
uspto-grants-1990_06
Patent number
US04935437

Reaction notes

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