(2E,4E)-3-Methyl-5-(2,6,6-triMethyl-1,3-cyclohexadien-1-yl)-2,4-pentadienenitrile synthesis

1synthesis methods

Product Name:(2E,4E)-3-Methyl-5-(2,6,6-triMethyl-1,3-cyclohexadien-1-yl)-2,4-pentadienenitrile
CAS Number:20109-91-5
Molecular formula:C15H19N
Molecular Weight:213.32

14398-35-7 Synthesis

(E)-4-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)but-3-en-2-one

14398-35-7
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21658-95-7 Synthesis

21658-95-7
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(2E,4E)-3-Methyl-5-(2,6,6-triMethyl-1,3-cyclohexadien-1-yl)-2,4-pentadienenitrile

20109-91-5
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Yield:20109-91-5 71%

Reaction Conditions:

Stage #1: diisopropyl (cyanomethyl)phosphonatewith sodium hydride in tetrahydrofuran at 0; for 0.5 h;
Stage #2: (3E)-4-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)but-3-en-2-one in tetrahydrofuran at 0 - 20; for 16 h;Further stages.;Horner-Emmons reaction;

References:

Wada, Akimori;Wang, Fei;Ito, Masayoshi [Chemical and Pharmaceutical Bulletin,2008,vol. 56,# 1,p. 112 - 114]