Thionyl Chloride → 3-(Chloromethyl)-5-phenylpyridine

HRID 349968노트

반응식

HRID 349968 반응식
[C:1]1([C:7]2[CH:8]=[C:9]([CH2:13]O)[CH:10]=[N:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:17])=O>>[Cl:17][CH2:13][C:9]1[CH:10]=[N:11][CH:12]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:8]=1

참가 물질

3

반응물 2

HCID 24386Thionyl ChlorideHCID 22254272(5-Phenylpyridin-3-yl)methanol

생성물 1

HCID 110849253-(Chloromethyl)-5-phenylpyridine수율 86%

실험 절차

A mixture of 5-phenyl-3-pyridylmethanol (4.50 g) and thionyl chloride (5 ml) was stirred at room temperature for 1 hour. After the reaction mixture was concentrated, saturated aqueous sodium bicarbonate solution was added to the mixture, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), and concentrated. The residue was subjected to silica gel column chromatography to obtain 3-chloromethyl-5-phenylpyridine (4.28 g, yield 86%) as colorless crystals from the fraction eluted with tetrahydrofuran. This was recrystallized from ethyl acetate-hexane. Melting point: 75–76° C.

후처리

  1. concentrationAfter the reaction mixture was concentrated
  2. additionsaturated aqueous sodium bicarbonate solution was added to the mixture, which
  3. extractionwas extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-583ccf24496241aa95ca1e2fff858437
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07179823B1

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