Thionyl Chloride → 3-(Chloromethyl)-2-isopropylpyridine

HRID 1689노트

반응식

HRID 1689 반응식
[CH:1]([C:4]1[C:9]([CH2:10]O)=[CH:8][CH:7]=[CH:6][N:5]=1)([CH3:3])[CH3:2].S(Cl)([Cl:14])=O>C(Cl)Cl>[CH:1]([C:4]1[C:9]([CH2:10][Cl:14])=[CH:8][CH:7]=[CH:6][N:5]=1)([CH3:3])[CH3:2]

참가 물질

4

반응물 2

HCID 24386Thionyl ChlorideHCID 19691012(2-Isopropylpyridin-3-yl)methanol

생성물 1

HCID 196910223-(Chloromethyl)-2-isopropylpyridine

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

The 2-isopropyl-3-hydroxymethylpyridine (240 mg, 1.59 mmol) was dissolved in CH2Cl2 (15 mL) and cooled under nitrogen to 0° C. and thionyl chloride (1.0 mL) was slowly added and the reaction was stirred for 3 hours. The solvent was removed under reduced pressure and the residue was partitioned between CH2Cl2 and saturated sodium bicarbonate. The organic layer was dried with MgSO4, filtered and the solvent removed under reduced pressure to give the desired 2-isopropyl-3-chloromethylpyridine. The 2-isopropyl-3-chloromethylpyridine (65 mg, 0.383 mmol) was dissolved in CHCl3 (10 mL) and cooled under nitrogen to 0° C. and m-chloroperbenzoic acid (55%, 150 mg) was added in small portions. The reaction was stirred for 2 hours. The solution was extracted with saturated aqueous sodium bicarbonate (2×5 mL). The organic phase was dried with MgSO4, filtered, and the solvent removed under reduced pressure. The residue was chromatographed on silica gel packed in 99:1 CH2Cl2 :MeOH and eluted with same. The appropriate fractions were combined and the solvent removed under reduced pressure to give the desired 2-isopropyl-3-chloromethylpyridine-N-oxide.

후처리

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was partitioned between CH2Cl2 and saturated sodium bicarbonate
  3. dry with materialThe organic layer was dried with MgSO4
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure

출처 및 근거

ORD 기록
ord-4bba085d9504420e80535135054ff927
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05726172

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