반응 #62142

반응 방정식

quinoline-2-carbaldehyde

benzoic acid methyl ester

sodium hydride

THF

→

title compound

4-(2-Quinolin-2-yl-ethyl)-benzoic acid methyl ester

용매

ethanol

반응 조건

후처리

1. 1
   기타The reaction mixture was quenched with brine
2. 2
   추출extracted with chloroform, dried magnesium sulfate
3. 3
   여과filtered
4. 4
   농축concentrated
5. 5
   기타to provide the crude alkene
6. 6
   workup.WAITAfter 40 min
7. 7
   여과the reaction mixture was filtered through celite and
8. 8
   농축concentrated
9. 9
   세척Biotage MPLC chromatography eluting with 10-20% ethyl acetate/hexane

실험 절차

To a solution of 4-[Triphenyl-phophanyl)-methyl]-benzoic acid methyl ester (1.87 g) in THF (16 ml) under N2 atmosphere at 0° C. was added sodium hydride (165 mg (60%)). After 30 min, quinoline-2-carbaldehyde (0.50 g) was added and the reaction stirred at ambient temperature for 2 h. The reaction mixture was quenched with brine, extracted with chloroform, dried magnesium sulfate, filtered and concentrated to provide the crude alkene. The crude product was placed on a parr shaker in ethanol (15 ml) with palladium hydroxide (200 mg) as the catalyst under 10 PSI of H2. After 40 min, the reaction mixture was filtered through celite and concentrated. Biotage MPLC chromatography eluting with 10-20% ethyl acetate/hexane provided the title compound. MS: (M+H m/z=292.1).

출처