TY - JOUR
T1 - Synthetic method of caffeic acid phenethyl ester by heck reaction
AU - Yang, Fengzhi
AU - Zhang, Man
AU - Xie, Jin
AU - Xie, Dongsheng
AU - Fu, Lei
N1 - Publisher Copyright:
©, 2015, Higher Education Press. All right reserved.
PY - 2015/5/10
Y1 - 2015/5/10
N2 - Many caffeic acid ester compounds are known because of their various pharmacological activities, with great commercial values such as medicine, health-care products and functional foods, especially caffeic acid phenethyl esters. Existing synthetic methods for caffeic acid esters, such as “acyl halide”, the alkylation, catalytic esterification, condensation agent method, Wittig reaction and Knoevenagel condensation, present certain limitation for their wide use. This research aims to explore a synthetic method with versatile conditions for caffeic acid esters by Heck reaction using commercially available materials. A total of three steps were operated to synthesize caffeic acid phenethyl ester (CAPE) protecting reaction, Heck reaction and de-protecting reaction, with 4-bromocatechol and acrylic acid phenethyl alcohol ester as starting materials. CAPE was obtained in a moderate yield of 40% under the optimized conditions of Heck reaction, which were V(Toluene):V(DMF)=4:1, Pd(OAc)2 (0.05 mmol), Ph3P (0.15 mmol), NEt3 (2 mmol), reaction temperature of 90 ℃ and reaction time of 24 h. Compared with the exising synthestic methods, the new method of constructing caffeic acid ester by Heck reaction developed in this work had advantages of versatile conditions, commercially available materials and simple synthetic steps.
AB - Many caffeic acid ester compounds are known because of their various pharmacological activities, with great commercial values such as medicine, health-care products and functional foods, especially caffeic acid phenethyl esters. Existing synthetic methods for caffeic acid esters, such as “acyl halide”, the alkylation, catalytic esterification, condensation agent method, Wittig reaction and Knoevenagel condensation, present certain limitation for their wide use. This research aims to explore a synthetic method with versatile conditions for caffeic acid esters by Heck reaction using commercially available materials. A total of three steps were operated to synthesize caffeic acid phenethyl ester (CAPE) protecting reaction, Heck reaction and de-protecting reaction, with 4-bromocatechol and acrylic acid phenethyl alcohol ester as starting materials. CAPE was obtained in a moderate yield of 40% under the optimized conditions of Heck reaction, which were V(Toluene):V(DMF)=4:1, Pd(OAc)2 (0.05 mmol), Ph3P (0.15 mmol), NEt3 (2 mmol), reaction temperature of 90 ℃ and reaction time of 24 h. Compared with the exising synthestic methods, the new method of constructing caffeic acid ester by Heck reaction developed in this work had advantages of versatile conditions, commercially available materials and simple synthetic steps.
KW - Caffeic acid phenethyl ester
KW - Heck reaction
KW - Synthesis
UR - http://www.scopus.com/inward/record.url?scp=84930151572&partnerID=8YFLogxK
U2 - 10.7503/cjcu20141076
DO - 10.7503/cjcu20141076
M3 - Article
AN - SCOPUS:84930151572
SN - 0251-0790
VL - 36
SP - 914
EP - 918
JO - Gaodeng Xuexiao Huaxue Xuebao/Chemical Journal of Chinese Universities
JF - Gaodeng Xuexiao Huaxue Xuebao/Chemical Journal of Chinese Universities
IS - 5
ER -