ChemicalBook CAS DataBase List 3-OXO-5-PHENYL-PENTANOIC ACID ETHYL ESTER

3-OXO-5-PHENYL-PENTANOIC ACID ETHYL ESTER synthesis

10synthesis methods

Product Name:3-OXO-5-PHENYL-PENTANOIC ACID ETHYL ESTER
CAS Number:17071-29-3
Molecular formula:C13H16O3
Molecular Weight:220.26

2033-24-1 Synthesis

2033-24-1
655 suppliers
$6.00/25g

645-45-4 Synthesis

645-45-4
344 suppliers
$15.00/5g

3-OXO-5-PHENYL-PENTANOIC ACID ETHYL ESTER

17071-29-3
18 suppliers
$175.00/50mg

Yield:17071-29-3 95%

Reaction Conditions:

with pyridine in ethanol;dichloromethane at 0 - 20; for 48.5 h;Reflux;

Steps:

1 5.1.1. Ethyl 3-oxo-5-phenylpentanoate (3)⁹

Hydrocinnamoyl chloride (11.2 mL, 75.6 mmol) was addeddropwise to a solution of Meldrum’s acid (10.9 g, 75.6 mmol) andpyridine (12.4 mL) in CH2Cl2 (140 mL) at 0 C. The solution wasstirred for 30 min at 0 C and then was allowed to room temperaturefor 24 h. The reaction mixture was washed with 10% aqueousHCl (2 50 mL) and H2O (50 mL) separately. The organic layer wasdried with MgSO4, filtered and concentrated under reduced pressure.The crude residue was dissolved in EtOH (100 mL) and heatedto reflux for 24 h. The mixture was concentrated under reducedpressure to give the dark oily residue which was purified by flashchromatography using EtOAc/petroleum ether (1:50 V/V) as theeluent to give required compound 3.Yield 95%; yellow liquid; 1H NMR (400 MHz, CDCl3) d (ppm)7.17-7.29 (m, 5H, ArH), 4.16 (q, J = 7.2 Hz, 2H, OCH2CH3), 3.41 (s,2H, COCH2CO), 2.85-2.92 (m, 4H, ArCH2CH2), 1.25 (t, J = 7.2 Hz,3H, OCH2CH3).

References:

Cao, Yuanyuan;Zhang, Yu;Wu, Shaotong;Yang, Quanzhi;Sun, Xuefeng;Zhao, Jianxiong;Pei, Fen;Guo, Ying;Tian, Chao;Zhang, Zhili;Wang, Haining;Ma, Liying;Liu, Junyi;Wang, Xiaowei [Bioorganic and Medicinal Chemistry,2015,vol. 23,# 1,p. 149 - 159]