Methanol → 1-(2-Chloro-4-pyridyl)-3-hydroxymethyl-6,7-diethoxynaphthalene

HRID 1740644

反応式

HRID 1740644 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([O:21][CH2:22][CH3:23])=[C:15]([O:18][CH2:19][CH3:20])[CH:16]=3)[CH:11]=[C:10]([C:24](O)=[O:25])[CH:9]=2)[CH:5]=[CH:4][N:3]=1.CO.[OH-].[Na+]>O1CCCC1>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([O:21][CH2:22][CH3:23])=[C:15]([O:18][CH2:19][CH3:20])[CH:16]=3)[CH:11]=[C:10]([CH2:24][OH:25])[CH:9]=2)[CH:5]=[CH:4][N:3]=1

参加物

5

反応物 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 220073981-(2-Chloro-4-pyridyl)-3-carboxy-6,7-diethoxynaphthalene

生成物 1

HCID 220073461-(2-Chloro-4-pyridyl)-3-hydroxymethyl-6,7-diethoxynaphthalene

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
50 °C

実験手順

To a suspension of 1-(2-chloro-4-pyridyl)-3-carboxy-6,7-diethoxynaphthalene in tetrahydrofuran (50 ml) is added dropwise a solution of 70% sodium aluminum bis(2-methoxyethoxy) hydride (70% toluene solution, 29.4 ml) in tetrahydrofuran (50 ml) at a temperature below 5° C. under nitrogen atmosphere, and the mixture is reacted at the same temperature for one hour. After the reaction is complete, to the mixture is added methanol (12 ml), and further thereto is added a 6.25 M aqueous sodium hydroxide solution (48 ml), and the mixture is stirred at 50° C. for one hour. The tetrahydrofuran layer is separated from the mixture, and the aqueous solution is extracted with methylene chloride, and the methylene chloride layer is separated, and combined with the tetrahydrofuran layer, then concentrated under reduced pressure. The resultant is extracted again with methylene chloride, washed, dried, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (solvent; chloroform:ethyl acetate=4:1), and crystallized from ether to give 1-(2-chloro-4-pyridyl)-3-hydroxymethyl-6,7-diethoxynaphthalene (3.94 g).

後処理

  1. customthe mixture is reacted at the same temperature for one hour
  2. customThe tetrahydrofuran layer is separated from the mixture
  3. extractionthe aqueous solution is extracted with methylene chloride
  4. customthe methylene chloride layer is separated
  5. concentrationconcentrated under reduced pressure
  6. extractionThe resultant is extracted again with methylene chloride
  7. washwashed
  8. customdried
  9. concentrationconcentrated under reduced pressure
  10. customThe residue is purified by silica gel column chromatography (solvent; chloroform:ethyl acetate=4:1)
  11. customcrystallized from ether

出典と根拠

ORDレコード
ord-7dc4719d2d8743f4b45b8d561d5bc40e
出典データセット
uspto-grants-1999_10
特許番号
US05969140

関連ノート

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