Реакция #1106642

ord-3b7a1f69344e4b4391f5ea65bae6d1bf

Уравнение реакции

[Na+].[OH-]
NaOH
COCOc1ccc(C(=O)CCc2ccc(OC)nc2)c(O)c1
1-(2-hydroxy-4-(methoxymethoxy)phenyl)-3-(6-methoxypyridin-3-yl)propan-1-one
O=C(O)C(F)(F)F
TFA
COc1ccc(CCC(=O)c2ccc(O)cc2O)cn1
white solid
Выход 35.8%
COc1ccc(CCC(=O)c2ccc(O)cc2O)cn1
2,4-dihydroxyphenyl-3-(6-methoxypyridin-3-yl)propan-1-one
Выход 35.8%

Растворители

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    ЭкстракцияThe aqueous was extracted with 100 ml EtOAc
  2. 2
    ПромывкаThe organic layer was washed with brine
  3. 3
    Сушкаdried (Na2SO4)
  4. 4
    Концентрированиеconcentrated
  5. 5
    ДругоеThe residue was purified by silica gel chromatography (15% EtOAc/Hexane)

Методика

To a solution of 1-(2-hydroxy-4-(methoxymethoxy)phenyl)-3-(6-methoxypyridin-3-yl)propan-1-one (1.62 g, 5.11 mmol) in CH3CN (30 ml) at room temperature was added TFA (2 ml) dropwise, two drops of water. The reaction was stirred at same temperature for 8 h. Aqueous 1N NaOH was added to the reaction mixture until pH=7. The aqueous was extracted with 100 ml EtOAc, and the organic layers were combined. The organic layer was washed with brine, dried (Na2SO4) and concentrated. The residue was purified by silica gel chromatography (15% EtOAc/Hexane) to provide 0.5 g (35%) of white solid.

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US08715761B2uspto-grants-2014_05