Thionyl Chloride → 2-(Benzyloxy)-6-(chloromethyl)pyridine

HRID 443289노트

반응식

HRID 443289 반응식
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15]O)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:19])=O>C1C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][Cl:19])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 24386Thionyl ChlorideHCID 21193214(6-(Benzyloxy)pyridin-2-yl)methanol

생성물 1

HCID 211931742-(Benzyloxy)-6-(chloromethyl)pyridine

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

A mixture of 2-benzyloxy-6-hydroxymethylpyridine (1.5 g, 7.0 mmol) and thionyl chloride (10 mL, 137 mmol) in benzene (25 mL) was stirred at room temp. overnight. The product mixture was concentrated under vacuum. The residue was partitioned between chloroform and aqueous sodium bicarbonate. The organic extract was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluting with 5% methanol in chloroform. Collection and concentration of appropriate fractions provided 2-benzyloxy-6-chloromethylpyridine as clear, colorless oil. This alkylating reagent was passed through a small plug of activated basic alumina immediately before use.

후처리

  1. concentrationThe product mixture was concentrated under vacuum
  2. customThe residue was partitioned between chloroform and aqueous sodium bicarbonate
  3. extractionThe organic extract
  4. washwas washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customCollection and concentration of appropriate fractions

출처 및 근거

ORD 기록
ord-b1199d2dc1974ab89c405153a163004d
출처 데이터셋
uspto-grants-1999_04
특허 번호
US05891889

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