Diethyl Ether → 2-Chloromethyl-6-phenoxypyridine

HRID 1194031노트

반응식

HRID 1194031 반응식
C(N(CC)CC)C.O[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:11]=1.C1(C)C=CC(S([Cl:32])(=O)=O)=CC=1.C(OCC)C>CN(C)C1C=CN=CC=1.ClCCl>[Cl:32][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:11]=1

참가 물질

7

반응물 4

HCID 3283Diethyl EtherHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 128791556-Phenoxy-2-pyridinemethanol

생성물 1

HCID 138492412-Chloromethyl-6-phenoxypyridine수율 62.6%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

Triethylamine (2.27 cm3) was added portionwise to a stirred solution of 2-hydroxymethyl-6-phenoxypyridine (3 g), para-toluenesulphonyl chloride (3.7 g), and 4-dimethylaminopyridine (1.17 g) in dichloromethane (30 cm3), whilst the reaction mixture was maintained at the ambient temperature (ca 22° C.) under an atmosphere of nitrogen. After a period of four hours, the reaction mixture was poured into diethyl ether, and washed sequentially with saturated aqueous sodium bicarbonate, water and brine. The organic layer was then dried, and after removal of the solvent by evaporation under reduced pressure, the crude crude product was subjected to column chromatography on silica gel using dichloromethane as eluent to give 2-chloromethyl-6-phenoxypyridine (2.05 g).

후처리

  1. washwashed sequentially with saturated aqueous sodium bicarbonate, water and brine
  2. customThe organic layer was then dried
  3. customafter removal of the solvent
  4. customby evaporation under reduced pressure

출처 및 근거

ORD 기록
ord-72fd4253575c404c8d2fa6772ab41b43
출처 데이터셋
uspto-grants-1989_03
특허 번호
US04812483

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