3-OXO-5-PHENYL-PENTANOIC ACID ETHYL ESTER synthesis
- 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
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645-45-4
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17071-29-3
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$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]
100-39-0
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141-97-9
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17071-29-3
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935254-77-6
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17071-29-3
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105-36-2
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645-59-0
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17071-29-3
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13148-05-5
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100-52-7
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17071-29-3
20 suppliers
$175.00/50mg