Thionyl Chloride → 2-(Chloromethyl)-5-methylpyridine

HRID 77894

반응식

HRID 77894 반응식
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8]O)=[N:6][CH:7]=1.S(Cl)([Cl:12])=O>C(Cl)Cl>[Cl:12][CH2:8][C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][N:6]=1

참가 물질

4

반응물 2

HCID 24386Thionyl ChlorideHCID 12325387(5-Methylpyridin-2-yl)methanol

생성물 1

HCID 5880562-(Chloromethyl)-5-methylpyridine수율 76%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A mixed solution of (5-methyl-pyridine-2-yl)-methanol (500 mg, 4.1 mmol) described in Manufacturing Example 11-1-1, thionyl chloride (0.59 mL, 8.1 mmol) and methylene chloride (10 mL) was stirred for 5 minutes under reflux. The reaction solution was cooled to room temperature and concentrated under a reduced pressure. The resulting residue was partitioned into diethyl ether and saturated sodium bicarbonate solution. The organic layer was separated and passed through a glass filter lined with silica gel (eluted with ethyl acetate). The eluate was concentrated to obtain the title compound (440 mg, 76%) as a crude product. The resulting compound was used in the following reaction without further purification.

후처리

  1. temperatureunder reflux
  2. concentrationconcentrated under a reduced pressure
  3. customThe resulting residue was partitioned into diethyl ether and saturated sodium bicarbonate solution
  4. customThe organic layer was separated
  5. filtrationfilter
  6. concentrationThe eluate was concentrated

출처 및 근거

ORD 기록
ord-0ce18b0b8ad34489bc176a56ffc7a334
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841327B2

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