تفاعل #324630

معادلة التفاعل

tributylphosphine

methyl 2-((S)-6-((R)-7-fluoro-4-(4-hydroxy-2,6-dimethylphenyl)-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetate

2-(methylthio)-ethanol

1,1′-(azodicarbonyl)-dipiperidine

→

title compound

Methyl 2-((S)-6-((R)-4-(2,6-dimethyl-4-(2-(methylthio)ethoxy)phenyl)-7-fluoro-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetate

المذيبات

toluene

ظروف التفاعل

المعالجة

1. 1
   أخرىpartitioned between saturated aqueous NaHCO3 solution and dichloromethane
2. 2
   workup.STIRRINGstirred for 30 minutes
3. 3
   أخرىThe phases are separated
4. 4
   تجفيفthe organic phase is dried (MgSO4)
5. 5
   أخرىThe solvents are evaporated
6. 6
   أخرىthe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 90:10→70:30)

الإجراء التجريبي

To a solution of methyl 2-((S)-6-((R)-7-fluoro-4-(4-hydroxy-2,6-dimethylphenyl)-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetate (280 mg) and 2-(methylthio)-ethanol (54 μL) in toluene (8 mL) are successively added 1,1′-(azodicarbonyl)-dipiperidine (240 mg) and tributylphosphine (240 mL). The mixture is stirred for 12 hours at room temperature, partitioned between saturated aqueous NaHCO3 solution and dichloromethane and stirred for 30 minutes. The phases are separated and the organic phase is dried (MgSO4). The solvents are evaporated and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 90:10→70:30) to give the title compound. Yield: 235 mg; LC (method 4): tR=1.97 min; Mass spectrum (ESI+): m/z=537 [M+H]+.

المصدر