تفاعل #40607

معادلة التفاعل

5-aminoindane

ethyl 3-chloropropionate

potassium carbonate

→

title compound

المردود 71.0%

3-(Indan-5-ylamino)-propionic acid ethyl ester

المردود 71.0%

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةAfter cooling to room temperature (rt)
2. 2
   استخلاصthe mixture was extracted into ethyl acetate (EtOAc)
3. 3
   غسيلwashed with water, brine
4. 4
   تجفيفdried with sodium sulfate (Na2SO4)
5. 5
   أخرىRemoval of the solvent and chromatography on silica
6. 6
   غسيلeluting with EtOAc/hexanes (1:20-1:10

الإجراء التجريبي

To a mixture of 5-aminoindane (5 g, 37.6 mmol), ethyl 3-chloropropionate (4.7 mL, 37.6 mmol) and potassium carbonate (5.2 g, 37.6 mmol) was added tetrabutylammonium bromide (200 mg). The mixture was stirred at 100° C. for 16 hours. After cooling to room temperature (rt), the mixture was extracted into ethyl acetate (EtOAc), washed with water, brine and then dried with sodium sulfate (Na2SO4). Removal of the solvent and chromatography on silica, eluting with EtOAc/hexanes (1:20-1:10, v/v), gave 6.2 g (71%) of the title compound. 1H NMR (300 MHz, CDCl3) δ (ppm): 7.03 (d, J=7.6 Hz, 1H), 6.55 (s, 1H), 6.43 (d, J=7.6 Hz, 1H), 4.15 (q, 2H), 3.86 (br, 1H), 3.43 (t, 2H), 2.82 (m, 4H), 2.60 (t, 2H), 2.06 (m, 2H), 1.27 (t, 3H).

المصدر