Chloromethyl Methyl Ether → 6-Chloro-2-fluoro-3-(methoxymethoxy)pyridine

HRID 455554ノート

反応式

HRID 455554 の反応式
[Cl:1][C:2]1[N:7]=[C:6]([F:8])[C:5]([OH:9])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:16](Cl)[O:17][CH3:18]>CC(C)=O>[Cl:1][C:2]1[N:7]=[C:6]([F:8])[C:5]([O:9][CH2:16][O:17][CH3:18])=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 7864Chloromethyl Methyl EtherHCID 11430Potassium CarbonateHCID 574756406-Chloro-2-fluoropyridin-3-ol

生成物 1

HCID 574756416-Chloro-2-fluoro-3-(methoxymethoxy)pyridine収率 82.3%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

反応条件

温度
60 °C

実験手順

A solution of 6-chloro-2-fluoropyridin-3-ol (1.4 Kg, 9.49 mol) was dissolved in acetone (13 L), and treated with K2CO3 (1574 g, 11.39 mol, 1.2 eq) and MOMCl (840 g, 10.44 mol, 1.1 eq). The mixture was heated at 60° C. for 2 hrs. After cooling to RT, the reaction mixture was filtered to remove inorganic salts. The filtrate was concentrated under reduced pressure. The residue was purified by flash column chromatography (0-10% EtOAc/hexanes), affording 6-chloro-2-fluoro-3-(methoxymethoxy)pyridine (1496 g) as a colorless oil in 80% yield over two steps.

後処理

  1. temperatureAfter cooling to RT
  2. filtrationthe reaction mixture was filtered
  3. customto remove inorganic salts
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by flash column chromatography (0-10% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-24d77b97b9ac422cb61dc1b27eddc73e
出典データセット
uspto-grants-2013_07
特許番号
US08497264B2

反応ノート

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