3-(Chloromethyl)pyridine hydrochloride → 3-(Diethoxyphosphorylmethyl)pyridine

HRID 52168

反応式

HRID 52168 の反応式
C([O-])(O)=O.[Na+].Cl.[N:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13]Cl)[CH:8]=1.[CH2:15]([O:17][P:18]([O:22]CC)[O:19][CH2:20][CH3:21])[CH3:16]>>[N:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][P:18](=[O:22])([O:19][CH2:20][CH3:21])[O:17][CH2:15][CH3:16])[CH:8]=1

参加物

4

反応物 3

HCID 233943-(Chloromethyl)pyridine hydrochlorideHCID 31215Triethyl phosphiteHCID 516892Sodium Bicarbonate

生成物 1

HCID 104626053-(Diethoxyphosphorylmethyl)pyridine収率 26.2%

反応条件

温度
85 °C

実験手順

To a stirred solution of saturated NaHCO3 was added 3-picolyl chloride hydrochloride (8.2 g, 50 mmol). After gas evolution ended, the mixture was extracted with CH2Cl2. The organic phase was dried (MgSO4) and concentrated in vacuo. To the resulting residue was added triethylphosphite (8.3 g, 50 mmol) and the neat mixture was stirred and heated at 85° C. overnight. The mixture was cooled and purified by flash column chromotography on silica gel eluting with 5% MeOH--CH2Cl2 to afford 3.0 g of diethyl 3-pyridylmethylphosphonate as a yellow oil.

後処理

  1. extractionthe mixture was extracted with CH2Cl2
  2. dry with materialThe organic phase was dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. temperatureThe mixture was cooled
  5. custompurified by flash column chromotography on silica gel eluting with 5% MeOH

出典と根拠

ORDレコード
ord-3480f0481a594e518e4e31c7f928693f
出典データセット
uspto-grants-1997_04
特許番号
US05616596

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