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

HRID 449724

반응식

HRID 449724 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8078Cyclohexane용매

반응 조건

온도
-78 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-31681f46521a48c08dceb685476077fa
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08481540B2

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