반응 #2320366

반응 방정식

{5-({[4-(methyloxy)phenyl]methyl}oxy)-4-[(phenyl methyl)oxy]-2-pyridinyl}methyl acetate

triphenylphosphine oxide

trifluoroacetic acid

triethylsilane

→

{5-Hydroxy-4-[(phenylmethyl)oxy]-2-pyridinyl}methyl acetate trifluoroacetate salt

용매

dichloromethane

dichloromethane

반응 조건

후처리

1. 1
   기타After 2 hours the mixture was evaporated
2. 2
   기타chromatographed on silica gel eluting with 50-100% ethyl acetate-hexane

실험 절차

A solution of {5-({[4-(methyloxy)phenyl]methyl}oxy)-4-[(phenyl methyl)oxy]-2-pyridinyl}methyl acetate (containing triphenylphosphine oxide as an impurity) (20 g, 50.8 mmol) in dichloromethane (500 ml) was treated with triethylsilane (10 ml, 62.6 mmol). A solution of trifluoroacetic acid (35 ml, 0.45 mol) in dichloromethane (200 ml) was added over 1 hour. After 2 hours the mixture was evaporated and chromatographed on silica gel eluting with 50-100% ethyl acetate-hexane, then 5-10% methanol-DCM affording a solid, the TFA salt in a 1:1 mixture with triphenylphosphine oxide (8.33 g).

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