반응 #81563

반응 방정식

6-Bromo-3,3-dimethyl-indan-1-one

methyl 4-vinylbenzoate

sodium bicarbonate

hexane

→

title compound

수율 70.0%

Methyl 4-[2-(1,1-dimethyl-3-oxo-indan-5-yl)vinyl]benzoate

수율 70.0%

용매

water

N,N-dimethylformamide

EtOAc

CH2Cl2

반응 조건

후처리

1. 1
   추출extracted with methylene chloride (50 mL×3)
2. 2
   건조The combined extracts were dried over magnesium sulfate
3. 3
   기타evaporated
4. 4
   기타The residue was purified by flash chromatography (CH2Cl2

실험 절차

6-Bromo-3,3-dimethyl-indan-1-one (1.20 g, 5.02 mmol), methyl 4-vinylbenzoate (1.63 g, 10.0 mmol), palladium acetate (56 mg, 0.25 mmol), tetrabutylammonium chloride hydrate (1.53 g, 5.52 mmol ), and sodium bicarbonate (1.05 g, 12.6 mmol) were stirred in 10 mL of anhydrous N,N-dimethylformamide at 80°-100° C. for 8 hours. The mixture was diluted with water (100 mL), extracted with methylene chloride (50 mL×3). The combined extracts were dried over magnesium sulfate and evaporated. The residue was purified by flash chromatography (CH2Cl2 :hexane=1:1 to 1:0, then CH2Cl2 :EtOAc=10:1) to give 1.12 g (70% yield) of the title compound as a yellow solid; 1H-NMR (CDCl3) δ1.45 (s, 6H), 2.64 (s, 2H), 5.30 (s, 3H), 7.18 (d, J=16.5 Hz, 1H), 7.26 (d, J=16.5 Hz, 1H), 7.52 (d, J=8.1 Hz, 1H), 7.58 (d, J=8.5 Hz, 2H), 7.78 (d, J=1.7, 8.1 Hz, 1H), 7.86 (d, J=1.7 Hz, 1H), 8.05 (d, J=8.5 Hz, 2H); MS m/e 321 (MH+).

출처