Acetone → 6-Chloro-2-fluoro-3-(methoxymethoxy)pyridine

HRID 931545ノート

反応式

HRID 931545 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:10]([O-:13])([O-])=O.[K+].[K+].[CH3:16]C(C)=O>>[Cl:1][C:2]1[N:7]=[C:6]([F:8])[C:5]([O:9][CH2:16][O:13][CH3:10])=[CH:4][CH:3]=1

参加物

4

反応物 3

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 574756406-Chloro-2-fluoropyridin-3-ol

生成物 1

HCID 574756416-Chloro-2-fluoro-3-(methoxymethoxy)pyridine収率 80%

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 MOMC1 (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-f9b58a0d451143c4860f2ab3100c82a2
出典データセット
uspto-grants-2016_03
特許番号
US09296759B2

反応ノート

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