5-{2'-[(E)-3-methoxymethylenoxyprop-1-enyl]cyclohex-1'-enyl}-2,3-dihydro[1,4]dioxine

Base Information

Chemical Name:5-{2'-[(E)-3-methoxymethylenoxyprop-1-enyl]cyclohex-1'-enyl}-2,3-dihydro[1,4]dioxine
CAS No.:952156-48-8
Molecular Formula:C₁₅H₂₂O₄
Molecular Weight:266.337
Hs Code.:

Synonyms:5-{2'-[(E)-3-methoxymethylenoxyprop-1-enyl]cyclohex-1'-enyl}-2,3-dihydro[1,4]dioxine

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Chemical Property of 5-{2'-[(E)-3-methoxymethylenoxyprop-1-enyl]cyclohex-1'-enyl}-2,3-dihydro[1,4]dioxine

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Technology Process of 5-{2'-[(E)-3-methoxymethylenoxyprop-1-enyl]cyclohex-1'-enyl}-2,3-dihydro[1,4]dioxine

There total 5 articles about 5-{2'-[(E)-3-methoxymethylenoxyprop-1-enyl]cyclohex-1'-enyl}-2,3-dihydro[1,4]dioxine 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: 77.0%

: 952156-47-7
(E)-3-[2'-(5,6-dihydro-[1,4]-dioxin-2-yl)cyclohex-1'-enyl]prop-2-en-1-ol

: 107-30-2
chloromethyl methyl ether

: 952156-48-8
5-{2'-[(E)-3-methoxymethylenoxyprop-1-enyl]cyclohex-1'-enyl}-2,3-dihydro[1,4]dioxine

Guidance literature:: With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃; for 2h;
DOI:10.1002/ejoc.200700201

Reference yield:

: 1056477-06-5,822-85-5
2-bromocyclohexanone

: 952156-48-8
5-{2'-[(E)-3-methoxymethylenoxyprop-1-enyl]cyclohex-1'-enyl}-2,3-dihydro[1,4]dioxine

Guidance literature:: Multi-step reaction with 5 steps

1.1: potassium bis(trimethylsilyl)amide / diethyl ether / 0.5 h / -78 °C

1.2: 94 percent / diethyl ether / 24 h / -78 - 22 °C

2.1: 82 percent / LiCl / tetrakis(triphenylphosphane)palladium / dimethylformamide / 14 h / 90 °C

3.1: 65 percent / NaOAc; nBu₄NBr / palladacycle / dimethylformamide; H₂O / 12 h / 105 °C

4.1: 85 percent / diisobutylaluminum hydride / toluene / 6 h / -78 - 22 °C

5.1: 77 percent / ethyldiisopropylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h / 0 - 20 °C

With dmap; tetrabutylammomium bromide; sodium acetate; potassium hexamethylsilazane; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; lithium chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; Palladacycle; In diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; 2.1: Stille coupling / 3.1: Heck reaction;
DOI:10.1002/ejoc.200700201

Reference yield:

: 952156-27-3
5-(2-bromocyclohex-1-en-1-yl)-2,3-dihydro-1,4-dioxine

: 952156-48-8
5-{2'-[(E)-3-methoxymethylenoxyprop-1-enyl]cyclohex-1'-enyl}-2,3-dihydro[1,4]dioxine

Guidance literature:: Multi-step reaction with 3 steps

1: 65 percent / NaOAc; nBu₄NBr / palladacycle / dimethylformamide; H₂O / 12 h / 105 °C

2: 85 percent / diisobutylaluminum hydride / toluene / 6 h / -78 - 22 °C

3: 77 percent / ethyldiisopropylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h / 0 - 20 °C

With dmap; tetrabutylammomium bromide; sodium acetate; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; Palladacycle; In dichloromethane; water; N,N-dimethyl-formamide; toluene; 1: Heck reaction;
DOI:10.1002/ejoc.200700201