Ethylene Glycol → 3-(Pyridin-4-yloxy)propan-1-OL

반응식

Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[CH2:8]([OH:11])[CH2:9]O.[OH-:12].[Na+].[CH3:14]S(C)=O>>[OH:12][CH2:14][CH2:9][CH2:8][O:11][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1

참가 물질

반응물 4

HCID 174Ethylene Glycol

HCID 679Dimethyl Sulfoxide

HCID 122884-Chloropyridine

HCID 14798Sodium Hydroxide

생성물 1

HCID 219360073-(Pyridin-4-yloxy)propan-1-OL수율 45%

반응 조건

온도: 100 °C

실험 절차

A mixture of 4-chloropyridine (7 g, 47 mmol), ethylene glycol (17.9 g, 235 mmol) and sodium hydroxide (4.67 g, 195 mmol) in DMSO (80 ml) was heated at 100° C. for 24 hours. Most of the solvent was removed by evaporation and the residue was diluted with ice water. The aqueous mixture was extracted with ethyl acetate, the extracts combined, dried (MgSO4) and the solvent removed by evaporation. The residue was purified by column chromatography eluting with methylene chloride/methanol mixtures (100/0 increasing to 97/3) to give 4-(3-hydroxypropoxy)pyridine (3.2 g, 45%).

후처리

customMost of the solvent was removed by evaporation
additionthe residue was diluted with ice water
extractionThe aqueous mixture was extracted with ethyl acetate
dry with materialdried (MgSO4)
customthe solvent removed by evaporation
customThe residue was purified by column chromatography
washeluting with methylene chloride/methanol mixtures (100/0 increasing to 97/3)

출처 및 근거

ORD 기록: ord-ce485901cf534c19a8dcbd1b815e3959
출처 데이터셋: uspto-grants-2000_06
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US06071921

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