반응 #50549

반응 방정식

phenylboric acid

toluene ethanol

Sodium carbonate

→

7-phenylisochroman-4-one

수율 70.0%

반응 조건

후처리

1. 1
   온도The solution was heated
2. 2
   온도at reflux for 18 h
3. 3
   기타evaporated
4. 4
   추출extracted with ethyl acetate (3×20 mL)
5. 5
   세척washed with brine
6. 6
   기타dried
7. 7
   기타evaporated
8. 8
   기타The solid was recrystallized from hexane

실험 절차

Nitrogen gas was bubbled through a mixture of the product of part e (0.611 g, 27 mmol) and phenylboric acid (0.36 g, 29 mmol) in 5:2 toluene/ethanol(30 mL) for 4 hours. Sodium carbonate (0.57 g, 5.38 mmol) was added followed by tetrabutylammonium bromide (0.049 g, 0.13 mmol) and tetrakis(triphenylphosphine)palladium (0.012 g, 0.04 mmol). The solution was heated at reflux for 18 h, cooled to room temperature, and evaporated. The residue was taken up in water (50 mL) and extracted with ethyl acetate (3×20 mL). The organics were combined, washed with brine, dried and evaporated. The solid was recrystallized from hexane to provide 0.429 g (70%) of 7-phenylisochroman-4-one as a gold-colored solid, mp 127°-128° C.: 1H NMR (CDCl3) δ8.12 (d, 1H), 7.60-7.66 (m, 3H), 7.39-7.51 (m, 4H), 4.96 (s, 2 H), 4.41 (s, 2H); IR (KBr) 1688 cm-1 ; Mass spectrum m/z=225 (M+H); Anal. calcd. for C15H12O2 : C 80.34, H 5.39; Found: C 80.03, H 5.45.

출처