Water → 6-[(4-Tert-butylphenyl)(cyclopentylmethoxy)methyl]-3-chloro-2-methoxypyridine

HRID 70718

反応式

HRID 70718 の反応式
[CH:1]1([CH2:6][OH:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:8]([C:12]1[CH:17]=[CH:16][C:15]([CH:18]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([O:27][CH3:28])[N:21]=2)O)=[CH:14][CH:13]=1)([CH3:11])([CH3:10])[CH3:9].O>ClCCCl.[Pd](Cl)Cl>[C:8]([C:12]1[CH:13]=[CH:14][C:15]([CH:18]([O:7][CH2:6][CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[C:20]2[N:21]=[C:22]([O:27][CH3:28])[C:23]([Cl:26])=[CH:24][CH:25]=2)=[CH:16][CH:17]=1)([CH3:11])([CH3:9])[CH3:10]

参加物

6

反応物 3

HCID 962WaterHCID 77195CyclopentanemethanolHCID 67396476(4-Tert-butylphenyl)(5-chloro-6-methoxypyridin-2-yl)methanol

生成物 1

HCID 673980526-[(4-Tert-butylphenyl)(cyclopentylmethoxy)methyl]-3-chloro-2-methoxypyridine収率 86%

試薬・触媒・溶媒 2

HCID 24290Palladium Chloride触媒HCID 111,2-Dichloroethane溶媒

反応条件

温度
80 °C

実験手順

Cyclopentylmethanol (0.039 mL) and palladium chloride (6.0 mg) were added to a solution of (4-tert-butylphenyl)(5-chloro-6-methoxypyridin-2-yl)methanol (110 mg) in 1,2-dichloroethane (2 mL) at room temperature, after which the mixture was stirred at 80° C. for six hours and then stirred at room temperature for two days. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate and filtered, after which the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1) to give 6-[(4-tert-butylphenyl)(cyclopentylmethoxy)methyl]-3-chloro-2-methoxypyridine as a pale red oil (112 mg, 86%).

後処理

  1. stirringstirred at room temperature for two days
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customafter which the solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1)

出典と根拠

ORDレコード
ord-7f44cb7813bb4de49faaf82451fc6b10
出典データセット
uspto-grants-2014_09
特許番号
US08822503B2

関連ノート

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