Thionyl Chloride → 3-(Chloromethyl)-2-methoxypyridine

HRID 1437905ノート

反応式

HRID 1437905 の反応式
S(Cl)([Cl:3])=O.[CH3:5][O:6][C:7]1[C:12]([CH2:13]O)=[CH:11][CH:10]=[CH:9][N:8]=1>ClCCl>[Cl:3][CH2:13][C:12]1[C:7]([O:6][CH3:5])=[N:8][CH:9]=[CH:10][CH:11]=1

参加物

4

反応物 2

HCID 24386Thionyl ChlorideHCID 10630565(2-Methoxypyridin-3-yl)methanol

生成物 1

HCID 149329453-(Chloromethyl)-2-methoxypyridine収率 86%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Thionyl chloride (9.5 mL, 130 mmol) was added portionwise to a solution of (2-methoxy-pyridin-3-yl)-methanol (1.02 g, 7.3 mmol) in dichloromethane (36 mL). The reaction mixture was stirred at room temperature overnight. The solvent was evaporated and dichloromethane (100 mL) was added. The solution was carefully treated with saturated aqueous sodium hydrogen carbonate and the mixture was stirred for 5-10 min. The organic layer was separated and the aqueous layer was extracted with dichloromethane (2×100 mL). The combined organic layers were washed with brine (100 mL), dried (sodium sulfate), filtered, and evaporated to give 3-chloromethyl-2-methoxy-pyridine (989 mg, 86%) as a light yellow oil.

後処理

  1. customThe solvent was evaporated
  2. additiondichloromethane (100 mL) was added
  3. additionThe solution was carefully treated with saturated aqueous sodium hydrogen carbonate
  4. stirringthe mixture was stirred for 5-10 min
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted with dichloromethane (2×100 mL)
  7. washThe combined organic layers were washed with brine (100 mL)
  8. dry with materialdried (sodium sulfate)
  9. filtrationfiltered
  10. customevaporated

出典と根拠

ORDレコード
ord-af9f06699f5145d6bcda6a6ba6dd1620
出典データセット
uspto-grants-2009_11
特許番号
US07622492B2

反応ノート

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