3-Pyridinecarboxaldehyde → 2-Methoxy-5-(pyrid-3-ylhydroxymethyl)pyridine

HRID 34912

反応式

HRID 34912 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1.C([Li])CCC.[N:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH:21]=[O:22])[CH:16]=1.[Cl-].[NH4+]>CCCCCC.CCOCC.O>[CH3:9][O:8][C:5]1[CH:4]=[CH:3][C:2]([CH:21]([C:17]2[CH:16]=[N:15][CH:20]=[CH:19][CH:18]=2)[OH:22])=[CH:7][N:6]=1

参加物

8

反応物 4

HCID 103713-PyridinecarboxaldehydeHCID 25517Ammonium ChlorideHCID 27348955-Bromo-2-methoxypyridineHCID 178418339Butyllithium

生成物 1

HCID 198517782-Methoxy-5-(pyrid-3-ylhydroxymethyl)pyridine収率 23.6%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒2 回HCID 8058Hexane溶媒

反応条件

温度
-50 °C

実験手順

5-Bromo-2-methoxypyridine (188 g) was added over 30 minutes to a 1.55 molar solution of n-butyllithium in hexane (770 ml) and ether (1200 ml) stirred at -50° C. The suspension was stirred for 1 hour when pyridine-3-carboxaldehyde (112 g) in ether (200 ml) was added over 30 minutes. The solution was stirred for 3.5 hr and then allowed to warm to ambient temperature. Saturated ammonium chloride solution (100 ml) and water (2 L) was added and the solution was concentrated to ca. 2.5 L in vacuo. Chloroform (3 L) was added and the title compound (41.3 g) was collected by filtration. The chloroform layer was separated, dried over magnesium sulphate and the solvent was removed under reduced pressure. The residue was treated with chloroform (200 ml) and filtered to give a second crop of the product (51.01 g). Recrystallisation from isopropanol/ether gave the title compound, m.p. 129°-130° C.

後処理

  1. additionwas added over 30 minutes
  2. stirringThe solution was stirred for 3.5 hr
  3. temperatureto warm to ambient temperature
  4. concentrationthe solution was concentrated to ca. 2.5 L in vacuo
  5. additionChloroform (3 L) was added
  6. filtrationthe title compound (41.3 g) was collected by filtration
  7. customThe chloroform layer was separated
  8. dry with materialdried over magnesium sulphate
  9. customthe solvent was removed under reduced pressure
  10. additionThe residue was treated with chloroform (200 ml)
  11. filtrationfiltered

出典と根拠

ORDレコード
ord-dc204285c2f4451f98963c40642279f0
出典データセット
uspto-grants-1988_08
特許番号
US04764519

関連ノート

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