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

Base Information

Chemical Name:(E)-3-[2'-(5,6-dihydro-[1,4]-dioxin-2-yl)cyclohex-1'-enyl]prop-2-en-1-ol
CAS No.:952156-47-7
Molecular Formula:C₁₃H₁₈O₃
Molecular Weight:222.284
Hs Code.:

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

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Chemical Property of (E)-3-[2'-(5,6-dihydro-[1,4]-dioxin-2-yl)cyclohex-1'-enyl]prop-2-en-1-ol

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Technology Process of (E)-3-[2'-(5,6-dihydro-[1,4]-dioxin-2-yl)cyclohex-1'-enyl]prop-2-en-1-ol

There total 4 articles about (E)-3-[2'-(5,6-dihydro-[1,4]-dioxin-2-yl)cyclohex-1'-enyl]prop-2-en-1-ol 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: 85.0%

: 952156-33-1
tert-butyl (E)-3-[2'-(5,6-dihydro-1,4-dioxin-2-yl)cyclohex-1'-enyl]acrylate

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

Guidance literature:: With diisobutylaluminium hydride; In toluene; at -78 - 22 ℃; for 6h;
DOI:10.1002/ejoc.200700201

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 4 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

With tetrabutylammomium bromide; sodium acetate; potassium hexamethylsilazane; diisobutylaluminium hydride; lithium chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; Palladacycle; In diethyl ether; 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

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

Guidance literature:: Multi-step reaction with 2 steps

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

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

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