Dimethylformamide → bis(4-Fluorophenyl)methyl(5-formyl-1H-1,2,4-triazol-1-ylmethyl)silane

HRID 568771

Reaction equation

HRID 568771 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([Si:8]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)([CH3:15])[CH2:9][N:10]2[CH:14]=[N:13][CH:12]=[N:11]2)=[CH:4][CH:3]=1.C([Li])CCC.CN([CH:31]=[O:32])C>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([Si:8]([C:16]2[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=2)([CH3:15])[CH2:9][N:10]2[C:14]([CH:31]=[O:32])=[N:13][CH:12]=[N:11]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 73675FlusilazoleHCID 178418339Butyllithium

Product 1

HCID 14154941bis(4-Fluorophenyl)methyl(5-formyl-1H-1,2,4-triazol-1-ylmethyl)silaneYield 80.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Bis(4-fluorophenyl)methyl(1H-1,2,4-triazol-1-ylmethyl)silane (1.3 g, 0.004 mol) was lithiated as described in Example 1 using 3.7 mL (0.0044 mol) of 1.2M n-butyllithium in 10 mL of THF. DMF (1.2 mL, 0.016 mol) was added and the solution was allowed to warm to 0° C. After 1 hour, the reaction mixture was diluted with 1:1 ether/hexanes, washed with 7% aqueous NaHCO3 and brine, dried over Na2SO4 and evaporated. Flash chromatography using 10% ether/methylene chloride gave 1.1 g of the title compound as a clear oil: nD 1.5612; ir (neat) 2840, 1705, 1587, 1499, 1228, 1160, 1106, 821 cm-1 ; nmr (CDCl3) δ, 0.7 (3H, s), 4.7 (2H, s), 7.0 (4H, t), 7.4 (4H, m), 7.9 (1H, s), 9.8 (1H, s).

Workup

  1. washwashed with 7% aqueous NaHCO3 and brine
  2. dry with materialdried over Na2SO4
  3. customevaporated

Sources & evidence

ORD record
ord-a4502ca3359746bba29aea7ceee88041
Source dataset
uspto-grants-1988_03
Patent number
US04729986

Linked notes

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