ethyl 4-cyano-4-(2,3-dihydro-8-methoxy-1,4-benzodioxin-5-yl)-3-cyclohexanecarboxylate

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Chemical Name:ethyl 4-cyano-4-(2,3-dihydro-8-methoxy-1,4-benzodioxin-5-yl)-3-cyclohexanecarboxylate
CAS No.:468730-61-2
Molecular Formula:C₁₉H₂₃NO₅
Molecular Weight:345.395
Hs Code.:

Synonyms:ethyl 4-cyano-4-(2,3-dihydro-8-methoxy-1,4-benzodioxin-5-yl)-3-cyclohexanecarboxylate

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Chemical Property of ethyl 4-cyano-4-(2,3-dihydro-8-methoxy-1,4-benzodioxin-5-yl)-3-cyclohexanecarboxylate

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Technology Process of ethyl 4-cyano-4-(2,3-dihydro-8-methoxy-1,4-benzodioxin-5-yl)-3-cyclohexanecarboxylate

There total 7 articles about ethyl 4-cyano-4-(2,3-dihydro-8-methoxy-1,4-benzodioxin-5-yl)-3-cyclohexanecarboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 48.0%

: 444108-39-8
ethyl 4-(2,3-dihydro-8-methoxy-1,4-benzodioxin-5-yl)-3-cyclohexenecarboxylate

: 7677-24-9
trimethylsilyl cyanide

: 444108-44-5
ethyl 4-cyano-4-(2,3-dihydro-8-methoxy-1,4-benzodioxin-5-yl)-3-cyclohexanecarboxylate

: 468730-61-2
ethyl 4-cyano-4-(2,3-dihydro-8-methoxy-1,4-benzodioxin-5-yl)-3-cyclohexanecarboxylate

Guidance literature:: trimethylsilyl cyanide; With trifluorormethanesulfonic acid; In 4-methyl-1,2,3-trifluorobenzene; at -20 ℃; for 0.0833333h; Inert atmosphere;

ethyl 4-(2,3-dihydro-8-methoxy-1,4-benzodioxin-5-yl)-3-cyclohexenecarboxylate; In 4-methyl-1,2,3-trifluorobenzene; at -20 - -10 ℃; for 8h; Inert atmosphere;
DOI:10.1021/ol902244e

Reference yield:

: 444108-39-8
ethyl 4-(2,3-dihydro-8-methoxy-1,4-benzodioxin-5-yl)-3-cyclohexenecarboxylate

: 7677-24-9
trimethylsilyl cyanide

: 444108-44-5
ethyl 4-cyano-4-(2,3-dihydro-8-methoxy-1,4-benzodioxin-5-yl)-3-cyclohexanecarboxylate

: 468730-61-2
ethyl 4-cyano-4-(2,3-dihydro-8-methoxy-1,4-benzodioxin-5-yl)-3-cyclohexanecarboxylate

: C₃₆H₄₄O₁₀

Guidance literature:: trimethylsilyl cyanide; With trifluorormethanesulfonic acid; In 4-methyl-1,2,3-trifluorobenzene; at -20 ℃; for 0.0833333h; Inert atmosphere;

ethyl 4-(2,3-dihydro-8-methoxy-1,4-benzodioxin-5-yl)-3-cyclohexenecarboxylate; In 4-methyl-1,2,3-trifluorobenzene; at -20 - -5 ℃; optical yield given as %de; Inert atmosphere;
DOI:10.1021/ol902244e

Reference yield:

: 190661-82-6
5-bromo-8-methoxy-2,3-dihydrobenzo[b][1,4]dioxine

: 444108-44-5
ethyl 4-cyano-4-(2,3-dihydro-8-methoxy-1,4-benzodioxin-5-yl)-3-cyclohexanecarboxylate

: 468730-61-2
ethyl 4-cyano-4-(2,3-dihydro-8-methoxy-1,4-benzodioxin-5-yl)-3-cyclohexanecarboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: n-butyllithium; Triisopropyl borate / tetrahydrofuran / -65 °C

2: 5% Pd(II)/C(eggshell); potassium carbonate; triphenylphosphine / 1,2-dimethoxyethane; water; ethyl acetate / 3 h / Inert atmosphere; Reflux

3: trifluorormethanesulfonic acid / 4-methyl-1,2,3-trifluorobenzene / 1 h / -20 °C / Inert atmosphere

With n-butyllithium; Triisopropyl borate; trifluorormethanesulfonic acid; 5% Pd(II)/C(eggshell); potassium carbonate; triphenylphosphine; In tetrahydrofuran; 1,2-dimethoxyethane; water; ethyl acetate; 4-methyl-1,2,3-trifluorobenzene; 2: Suzuki-Miyaura coupling;
DOI:10.1021/op1001287