反応 #43946

反応方程式

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

収率 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

収率 82.0%

溶媒

Hexane

toluene

反応条件

後処理

1. 1
   ろ過the precipitated insoluble substance was filtered off
2. 2
   濃縮the filtrate was concentrated under reduced pressure
3. 3
   その他The residue was purified by silica gel column chromatography (ethyl acetate:hexane=30:70-80:20)

実験手順

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.

出典