Chlorotrimethylsilane → 6-Chloro-3-methoxy-4-trimethylsilanyl-pyridazine

HRID 449724

反応式

HRID 449724 の反応式
C(NC(C)C)(C)C.C([Li])CCC.[Cl:13][C:14]1[N:15]=[N:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=1.Cl[Si:23]([CH3:26])([CH3:25])[CH3:24]>C1CCCCC1.O1CCCC1>[Cl:13][C:14]1[N:15]=[N:16][C:17]([O:20][CH3:21])=[C:18]([Si:23]([CH3:26])([CH3:25])[CH3:24])[CH:19]=1

参加物

7

反応物 4

HCID 6397ChlorotrimethylsilaneHCID 7912DiisopropylamineHCID 744033-Chloro-6-methoxypyridazineHCID 178418339Butyllithium

生成物 1

HCID 104659176-Chloro-3-methoxy-4-trimethylsilanyl-pyridazine

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8078Cyclohexane溶媒

反応条件

温度
-78 °C

実験手順

In a 2-necked round bottom flask under argon placed 4.0476 g of distilled diisopropylamine and 60 mL of tetrahydrofuran (Aldrich, anhydrous, no stabilizer). The mixture was cooled to −78° C., then ca 20 mL of 2.0 M butyl lithium in cyclohexane was added. The mixture was set in an ice bath for 20 minutes, then cooled to −78° C. and a solution of 2.8912 g of 3-chloro-6-methoxy-pyridazine and 3.05 mL of chlorotrimethyl silane in 12 mL of tetrahydrofuran was added over 15 minutes. The mixture was stirred for 2 hours (a deep red color formed, then faded to yellow), then quenched by the addition of 10 mL of saturated sodium dihydrogen phosphate solution. The mixture was taken up in 350 mL of ethyl acetate, washed 1×75 mL brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure.

後処理

  1. customIn a 2-necked round bottom flask under argon placed
  2. temperaturecooled to −78° C.
  3. customformed
  4. customthen quenched by the addition of 10 mL of saturated sodium dihydrogen phosphate solution
  5. washwashed 1×75 mL brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-31681f46521a48c08dceb685476077fa
出典データセット
uspto-grants-2013_07
特許番号
US08481540B2

関連ノート

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