反応 #1449734

反応方程式

(2E,4E)-5-(2-nitrophenyl)penta-2,4-dienoic acid

tetrahydrofuran

triethylamine

methyl 6-aminohexanoate hydrochloride

→

title compound

収率 89.5%

(2E,4E)-6-[5-(2-Nitrophenyl)penta-2,4-dienoylamino]hexanoic acid methyl ester

収率 89.5%

反応条件

後処理

1. 1
   その他The solvent was evaporated, to the obtained residue water (15 ml)
2. 2
   workup.ADDITIONwas added
3. 3
   ろ過the precipitate was filtered off
4. 4
   洗浄The precipitate was washed with an additional amount of water
5. 5
   その他dried

実験手順

To a solution of (2E,4E)-5-(2-nitrophenyl)penta-2,4-dienoic acid (9a) (0.44 g, 2.0 mmol) in dry tetrahydrofuran (10 ml) 1,1′-carbonyldiimidazole (0.36 g, 2.2 mmol) (Sigma-Aldrich) was added and the mixture was stirred for 1 hour at ambient temperature. To the reaction mixture triethylamine (0.30 g 3.0 mmol) and methyl 6-aminohexanoate hydrochloride (10) (0.40 g, 2.2 mmol) successively were added and the resultant suspension was stirred for 6 hour at ambient temperature. The solvent was evaporated, to the obtained residue water (15 ml) was added and the precipitate was filtered off. The precipitate was washed with an additional amount of water and dried to give the title compound (0.62 g, 89%) as a yellow solid, m.p. 115-117° C. 1H NMR (DMSO-d6, HMDSO), δ: 1.10-1.79 (6H, m, CH2); 2.29 (2H, J=7.0 Hz, CH2); 3.17 (2H, q, J=5.6 Hz, CH2N); 3.60 (3H, s); 6.24 (1H, d, J=14.8 Hz, CH); 7.04-8.10 (8H, m, CH—CH═CH, C6H4, NH).

出典