反応 #1844459

反応方程式

hydrogen

bromomethyl

methyl 4'-(bromomethyl)biphenyl-2-carboxylate

Sodium hydride

2-ethyl-4-quinolone

→

methyl 4'-[(2-ethylquinolin-4-yloxy)methyl]biphenyl-2-carboxylate

収率 64.5%

methyl 4'-[(2-ethylquinolin-4-yloxy)methyl]biphenyl-2- carboxylate

収率 64.5%

溶媒

N,N-dimethylformamide

DMF

反応条件

後処理

1. 1
   その他prepared by the method
2. 2
   その他The solvent was removed by evaporation
3. 3
   その他the residue was partitioned between water (10 ml) and ethyl acetate (2×5 ml)
4. 4
   洗浄The organic phase was washed with water
5. 5
   乾燥dried (MgSO4)
6. 6
   その他The solvent was evaporated
7. 7
   その他the residue purified by flash chromatography
8. 8
   洗浄eluting with ethyl acetate/dichloromethane (1:4 v/v)

実験手順

Sodium hydride (60% dispersion in mineral oil; 60 mg) was added to a stirred solution of 2-ethyl-4-quinolone (260 mg) prepared by the method described in Org. Syn., 1955, Coll. Vol. III, p.374 and p593), in N,N-dimethylformamide (DMF)(2.5 ml). The mixture was stirred until evolution of hydrogen had ceased and then a solution of the bromomethyl compound (C) (460 mg) in DMF (1 ml) was added. The reaction mixture was stirred for 16 hours. The solvent was removed by evaporation and the residue was partitioned between water (10 ml) and ethyl acetate (2×5 ml). The organic phase was washed with water, followed by saturated sodium chloride solution and dried (MgSO4). The solvent was evaporated and the residue purified by flash chromatography, eluting with ethyl acetate/dichloromethane (1:4 v/v) to give methyl 4'-[(2-ethylquinolin-4-yloxy)methyl]biphenyl-2-carboxylate (A) as a solid (385 mg), m.p. 132°-134° C.; NMR: 1.41(t,3H), 2.97(q,2H), 3.68(s,3H), 5.34(s,2H), 6.77(s,1H), 7.44-7.7(complex m,9H), 7.87(dd,1H), 8.0(d,1H), 8.26(dd,1H); mass spectrum (positive chemical ionisation [+ve CI]: 398 (M+H)+, 225, 174; 13C NMR: (benzylic CH2) 69.73.

出典