Methyl iodide → HCID 13474686, compound

HRID 1980521Notes

Reaction equation

HRID 1980521 reaction equation
[C:1]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:6]=[CH:5][C:4]([Si:7]([CH3:15])([CH3:14])[CH2:8][N:9]2[CH:13]=[N:12][CH:11]=[N:10]2)=[CH:3][CH:2]=1.[CH2:22]([Li])CCC.CI>O1CCCC1.CCCCCC.O>[C:1]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:2]=[CH:3][C:4]([Si:7]([CH3:15])([CH3:14])[CH2:8][N:9]2[C:13]([CH3:22])=[N:12][CH:11]=[N:10]2)=[CH:5][CH:6]=1

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 13474675(1,1'-biphenyl-4-yl)dimethyl(1H-1,2,4-triazol-1-ylmethyl)silaneHCID 178418339Butyllithium

Product 1

HCID 13474686HCID 13474686, compoundYield 92.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

A solution of 5.9 g (0.020 mol) of (1,1'-biphenyl-4-yl)dimethyl(1H-1,2,4-triazol-1-ylmethyl)silane in 40 ml of dry tetrahydrofuran was chilled to -40° under N2 and stirred while 12.5 ml (0.020 mol) of 1.6 molar n-butyllithium in hexane was added dropwise. The resulting yellow solution was stirred another 15 minutes at -40°, treated with 1.9 ml (4.2 g, 0.030 mol) of methyl iodide, and allowed to warm to room temperature. The resulting solution was diluted with water and extracted with hexanes. Washing the organic extracts with water and brine, drying over magnesium sulfate, and evaporation give 5.7 g of solid, which was purified by dry-column chromatography over silica gel (ethyl acetate elution) to give 1.1 g of crude product. Recrystallization from 12 ml of 3:1 hexanesethyl acetate then gave 0.97 g (16%) of the title compound as an off white solid: m.p. 95°-98°; ir (Nujol® ) 1590, 1270, 1250, 1180, 1120, 830, 765, 700 cm-1 ; nmr (CDCl3) 0.5 (6H, s), 2.2 (3H, s), 3.7 (2H, s), 7.2-7.7 (9H, m), 7.8 (1H, s).

Workup

  1. additionwas added dropwise
  2. extractionextracted with hexanes
  3. washWashing the organic extracts with water and brine
  4. dry with materialdrying over magnesium sulfate, and evaporation

Sources & evidence

ORD record
ord-db2d2112a49a46feb0b0d6cac0ed28a2
Source dataset
uspto-grants-1985_04
Patent number
US04510136

Reaction notes

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