Acetic Acid → 4-Oxo-6-phenyl-hex-5-enoic acid ethyl ester

HRID 852890Notes

Reaction equation

HRID 852890 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]([O:16][CH2:17][CH3:18])(=[O:15])[CH2:10][CH2:11][C:12]([CH3:14])=[O:13].C(O)(=O)C.N1CCCCC1>C1C=CC=CC=1.CCOCC>[CH2:17]([O:16][C:9](=[O:15])[CH2:10][CH2:11][C:12](=[O:13])[CH:14]=[CH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH3:18]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 8082PiperidineHCID 10883Ethyl levulinate

Product 1

HCID 694193024-Oxo-6-phenyl-hex-5-enoic acid ethyl esterYield 95%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent

Procedure

Benzaldehyde 69a (5.40 g, 50 mmol) and ethyl levulinate 97 (7.21 g, 50 mmol) were dissolved in benzene (25 mL) then glacial acetic acid (6 mL) and piperidine (2 mL) were added. The solution was stirred and refluxed under a Dean-Stark trap under argon for 5 hr. The solution was cooled and diluted with ether and washed twice with 2M HCl, 5% NaHCO3 brine and evaporated to give an oil 11.0 g, 95%. 1H NMR (300 MHz, CDCl3) δ 1.27, 3H, t(J 7.1); 2.69, 2H, t(J 6.7); 3.02, 2H, t(J 6.7); 4.16, 2H, q(J 7.1); 6.77, 1H, d(J 16.2); 7.37-7.43, 3H, m; 7.51-7.60, 2H, m; 7.60, 1H, d(J 16.4). 13C NMR (CDCl3) 14.2, 28.2, 35.2, 60.7, 125.8, 128.3, 128.9, 130.5, 134.4, 142.9, 172.9, 198.1.

Workup

  1. temperaturerefluxed under a Dean-Stark trap under argon for 5 hr
  2. temperatureThe solution was cooled
  3. washwashed twice with 2M HCl, 5% NaHCO3 brine
  4. customevaporated

Sources & evidence

ORD record
ord-37a150a47cb7466892c1eab3fe00dddd
Source dataset
uspto-grants-2007_08
Patent number
US07253194B2

Reaction notes

Loading…