Reaktion #43930

Reaktionsgleichung

1,1′-(azodicarbonyl)dipiperidine

methyl[(3S)-6-hydroxy-2,3-dihydro-1-benzofuran-3-yl]acetate

(3′-(hydroxymethyl)-6-methyl-4-[3-(methylsulfonyl)propoxy]biphenyl-2-yl)methyl acetate

tributylphosphine

→

title compound

Ausbeute 79.0%

Methyl[(3S)-6-({2′-(acetoxymethyl)-6′-methyl-4′-[3-(methylsulfonyl)propoxy]biphenyl-3-yl}methoxy)-2,3-dihydro-1-benzofuran-3-yl]acetate

Ausbeute 79.0%

Lösungsmittel

Hexane

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationthe precipitated insoluble substance was filtered off
2. 2
   Einengenthe filtrate was concentrated under reduced pressure
3. 3
   SonstigeThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=30:70-70:30)

Vorschrift

A solution of methyl[(3S)-6-hydroxy-2,3-dihydro-1-benzofuran-3-yl]acetate (0.208 g, 1.00 mmol), (3′-(hydroxymethyl)-6-methyl-4-[3-(methylsulfonyl)propoxy]biphenyl-2-yl)methyl acetate (0.360 g, 1.00 mmol) and tributylphosphine (0.324 g, 1.60 mmol) in toluene (15 mL) was stirred, 1,1′-(azodicarbonyl)dipiperidine (0.404 g, 1.60 mmol) was added, and the mixture was stirred at room temperature for 3 hr under nitrogen atmosphere. Hexane (8 mL) was added to the reaction mixture, the precipitated insoluble substance was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=30:70-70:30) to give the title compound (0.432 g, yield 79%) as a colorless oil.

Quelle