Dimethyl Disulfide → bis(4-Fluorophenyl)methyl(5-methylthio-1H-1,2,4-triazol-1-ylmethyl)silane

HRID 568774

反応式

HRID 568774 の反応式
[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.[CH3:28][S:29]SC>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]([S:29][CH3:28])=[N:13][CH:12]=[N:11]2)=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 12232Dimethyl DisulfideHCID 73675FlusilazoleHCID 178418339Butyllithium

生成物 1

HCID 14154947bis(4-Fluorophenyl)methyl(5-methylthio-1H-1,2,4-triazol-1-ylmethyl)silane収率 77.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 1.5 g (0.005 mol) of bis(4-fluorophenyl)methyl(1H-1,2,4-triazol-1-ylmethyl)silane in 10 mL of THF was treated with n-butyllithium as described in Example 1. To this solution was added 0.63 mL (0.007 mol) of dimethyl disulfide. The reaction mixture was allowed to warm to 0°, stirred 30 minutes, then poured into 1:1 ether/hexanes, washed with 7% aqueous NaHCO3 and brine, dried over Na2SO4, filtered and evaporated. The crude product was flash chromatographed (5% ether/methylene chloride) to give 1.4 g of the title compound as a clear oil: nD 1.5750; ir (neat) 3030 (w), 2935 (w), 1587, 1496, 1230, 1160, 1106, 1035, 822 cm-1 ; nmr (CDCl3) δ 0.7 (3H, s), 2.6 (3H, s), 4.0 (2H, s), 7.1 (4H, m), 7.5 (4H, m), 7.8 (1 H, s).

後処理

  1. temperatureto warm to 0°
  2. washwashed with 7% aqueous NaHCO3 and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customchromatographed (5% ether/methylene chloride)

出典と根拠

ORDレコード
ord-b35502fe5bdf4464be34b6a91fa779c7
出典データセット
uspto-grants-1988_03
特許番号
US04729986

関連ノート

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