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

HRID 443289ノート

反応式

HRID 443289 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b1199d2dc1974ab89c405153a163004d
出典データセット
uspto-grants-1999_04
特許番号
US05891889

反応ノート

読み込み中…