(+/-)-[1-(8-tert-butoxy-2-hydroxy-3-octynyl)-2,5-cyclohexadiene-1-yl]methyl pivalate

Base Information

Chemical Name:(+/-)-[1-(8-tert-butoxy-2-hydroxy-3-octynyl)-2,5-cyclohexadiene-1-yl]methyl pivalate
CAS No.:245672-16-6
Molecular Formula:C₂₄H₃₈O₄
Molecular Weight:390.563
Hs Code.:

Synonyms:(+/-)-[1-(8-tert-butoxy-2-hydroxy-3-octynyl)-2,5-cyclohexadiene-1-yl]methyl pivalate

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Chemical Property of (+/-)-[1-(8-tert-butoxy-2-hydroxy-3-octynyl)-2,5-cyclohexadiene-1-yl]methyl pivalate

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Technology Process of (+/-)-[1-(8-tert-butoxy-2-hydroxy-3-octynyl)-2,5-cyclohexadiene-1-yl]methyl pivalate

There total 8 articles about (+/-)-[1-(8-tert-butoxy-2-hydroxy-3-octynyl)-2,5-cyclohexadiene-1-yl]methyl pivalate 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:

: 121587-75-5
tert-butyl 5-hexynyl ether

: 245672-15-5
[1-(formylmethyl)-2,5-cyclohexadiene-1-yl]methyl pivalate

: 245672-16-6
(+/-)-[1-(8-tert-butoxy-2-hydroxy-3-octynyl)-2,5-cyclohexadiene-1-yl]methyl pivalate

Guidance literature:: tert-butyl 5-hexynyl ether; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.5h;

[1-(formylmethyl)-2,5-cyclohexadiene-1-yl]methyl pivalate; In tetrahydrofuran; for 1h;
DOI:10.1016/S0040-4020(99)00455-X

Reference yield:

: 3282-30-2
pivaloyl chloride

: 245672-16-6
(+/-)-[1-(8-tert-butoxy-2-hydroxy-3-octynyl)-2,5-cyclohexadiene-1-yl]methyl pivalate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 87 percent / 4-DMAP; Et₃N / CH₂Cl₂ / 54 h / 20 °C

2.1: FeCl₃ / 0.25 h

3.1: 12.5 g / aq. NaOH / methanol / 0.5 h / 15 °C

4.1: 96 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂

5.1: n-BuLi / tetrahydrofuran / 0.5 h / -78 °C

5.2: 7.49 g / tetrahydrofuran / 1 h

With dmap; sodium hydroxide; n-butyllithium; oxalyl dichloride; iron(III) chloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; 1.1: Esterification / 2.1: Elimination / 3.1: Deacetylation / 4.1: Oxidation / 5.1: Metallation / 5.2: Addition;
DOI:10.1016/S0040-4020(99)00455-X

Reference yield:

: 245672-12-2
1-(2-tert-butoxyethyl)-2,5-cyclohexadiene-1-methanol

: 245672-16-6
(+/-)-[1-(8-tert-butoxy-2-hydroxy-3-octynyl)-2,5-cyclohexadiene-1-yl]methyl pivalate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 87 percent / 4-DMAP; Et₃N / CH₂Cl₂ / 54 h / 20 °C

2.1: FeCl₃ / 0.25 h

3.1: 12.5 g / aq. NaOH / methanol / 0.5 h / 15 °C

4.1: 96 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂

5.1: n-BuLi / tetrahydrofuran / 0.5 h / -78 °C

5.2: 7.49 g / tetrahydrofuran / 1 h

With dmap; sodium hydroxide; n-butyllithium; oxalyl dichloride; iron(III) chloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; 1.1: Esterification / 2.1: Elimination / 3.1: Deacetylation / 4.1: Oxidation / 5.1: Metallation / 5.2: Addition;
DOI:10.1016/S0040-4020(99)00455-X