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

HRID 70718

반응식

HRID 70718 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 24290Palladium Chloride촉매HCID 111,2-Dichloroethane용매

반응 조건

온도
80 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-7f44cb7813bb4de49faaf82451fc6b10
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822503B2

연결된 노트

불러오는 중…