Reaktion #43946

Reaktionsgleichung

1,1′-(azodicarbonyl)dipiperidine

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

{2′,3′,5′,6′-tetramethyl-4′-[3-(methylsulfonyl)propoxy]biphenyl-3-yl}methanol

tributylphosphine

→

title compound

Ausbeute 82.0%

Methyl[(3S)-6-({2′,3′,5′,6′-tetramethyl-4′-[3-(methylsulfonyl)propoxy]biphenyl-3-yl}methoxy)-2,3-dihydro-1-benzofuran-3-yl]acetate

Ausbeute 82.0%

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=30:70-80:20)

Vorschrift

A solution of methyl[(3S)-6-hydroxy-2,3-dihydro-1-benzofuran-3-yl]acetate (0.208 g, 1.00 mmol), {2′,3′,5′,6′-tetramethyl-4′-[3-(methylsulfonyl)propoxy]biphenyl-3-yl}methanol (0.377 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 1.5 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=30:70-80:20) to give the title compound (0.462 g, yield 82%) as a colorless oil.

Quelle