2-Hexenoic acid, 6-bromo-, ethyl ester, (E)- synthesis
- Product Name:2-Hexenoic acid, 6-bromo-, ethyl ester, (E)-
- CAS Number:71032-10-5
- Molecular formula:C8H13BrO2
- Molecular Weight:221.0916
Yield:71032-10-5 100%
Reaction Conditions:
in dichloromethane at 20;Inert atmosphere;
Steps:
Ethyl (E)-6-bromohex-2-enoate (19)
A solution of 4-bromobutanal (21.4 g, 140 mmol) and ethyl (triphenylphosphoranylidene)acetate(46.0 g, 140 mmol) in CH2Cl2 (100 mL) was stirred at r.t. overnight. The mixture was concentratedand the residue was triturated with hexane and filtered. The filtrate was concentrated to give the titlecompound as a yellow oil which was used in the following step without further purification (~47 g,quantitative); 1H NMR (300 MHz, CDCl3) d 6.93 (m, 1H, CH2 CH=CH), 5.88 (d, J = 15.9 Hz, 1H,CHOOCH3), 4.28 (t, J = 6.4 Hz, 2H, CH2Br), 4.12 (q, J = 11.4, 7.1 Hz, 2H, OCH2), 2.39 (m, 2H,CH2CH=CH), 2.02 (m, 2H, CH2CH2Br), 1.25 (t, J = 6.8 Hz, CH3); spectroscopic data in accordancewith literature values.3
References:
Bhadbhade, Mohan;Daryl Ariawan, A.;Ho, Junming;Hunter, Luke;Mansour, Flora;Richardson, Nicole [Molecules,2021,vol. 26,# 13,art. no. 3974] Location in patent:supporting information
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