Water → 2-Chloro-3-(prop-2-yn-1-yloxy)pyridine

HRID 27037

反応式

HRID 27037 の反応式
[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[OH-].[K+].[CH2:11](Cl)[C:12]#[CH:13].O>CN(C=O)C.CCOCC>[Cl:1][C:2]1[C:7]([O:8][CH2:13][C:12]#[CH:11])=[CH:6][CH:5]=[CH:4][N:3]=1

参加物

7

反応物 4

HCID 962WaterHCID 122213-Chloro-1-propyneHCID 14797Potassium HydroxideHCID 811362-Chloro-3-pyridinol

生成物 1

HCID 233434882-Chloro-3-(prop-2-yn-1-yloxy)pyridine収率 52.2%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
15 °C

実験手順

To a solution of 15.6 g (0.12 mole) 2-chloro-3-pyridinol in 200 ml DMF were added 6.7 g (0.12 mole) powdered potassium hydroxide. After cooling to 15° C., 9.0 g (0.12 mole) propargyl chloride was added dropwise. This mixture was stirred at room temperature for 2 hrs., then 200 ml water and 400 ml ether were added. After agitating, the organic layer was separated, dried over anhydrous magnesium sulfate, filtered and concentrated to leave 16.0 g crude product. Recrystallization from hexane gave 10.5 g pure 2-chloro-3-(2-propynyloxy)pyridine, mp 78°-79°.

後処理

  1. stirringAfter agitating
  2. customthe organic layer was separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto leave 16.0 g crude product
  7. customRecrystallization from hexane

出典と根拠

ORDレコード
ord-1266bcf6f3ac417eb2ed36367379b475
出典データセット
uspto-grants-1980_09
特許番号
US04220577

関連ノート

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