2-(tert-butyl-dimethyl-silanyloxymethyl)-5-(4-methoxy-benzyloxy)-3-methyl-pent-2-en-1-ol

Base Information

Chemical Name:2-(tert-butyl-dimethyl-silanyloxymethyl)-5-(4-methoxy-benzyloxy)-3-methyl-pent-2-en-1-ol
CAS No.:554416-42-1
Molecular Formula:C₂₁H₃₆O₄Si
Molecular Weight:380.6
Hs Code.:

2-(<i>tert</i>-butyl-dimethyl-silanyloxymethyl)-5-(4-methoxy-benzyloxy)-3-methyl-pent-2-en-1-ol

Synonyms:2-(tert-butyl-dimethyl-silanyloxymethyl)-5-(4-methoxy-benzyloxy)-3-methyl-pent-2-en-1-ol

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Chemical Property of 2-(tert-butyl-dimethyl-silanyloxymethyl)-5-(4-methoxy-benzyloxy)-3-methyl-pent-2-en-1-ol

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Technology Process of 2-(tert-butyl-dimethyl-silanyloxymethyl)-5-(4-methoxy-benzyloxy)-3-methyl-pent-2-en-1-ol

There total 7 articles about 2-(tert-butyl-dimethyl-silanyloxymethyl)-5-(4-methoxy-benzyloxy)-3-methyl-pent-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: 66.0%

: 554416-26-1
2-(tert-butyl-dimethyl-silanyloxymethyl)-5-(4-methoxy-benzyloxy)-3-methyl-pent-2-enoic acid methyl ester

: 554416-42-1
2-(tert-butyl-dimethyl-silanyloxymethyl)-5-(4-methoxy-benzyloxy)-3-methyl-pent-2-en-1-ol

Guidance literature:: With diisobutylaluminium hydride; In toluene; at -78 ℃; for 1.5h;
DOI:10.1016/S0040-4020(03)00372-7

Reference yield:

: 70887-29-5
4-methoxybenzyl iodide

: 554416-42-1
2-(tert-butyl-dimethyl-silanyloxymethyl)-5-(4-methoxy-benzyloxy)-3-methyl-pent-2-en-1-ol

Guidance literature:: Multi-step reaction with 7 steps

1.1: 68 percent / sodium hydride / tetrahydrofuran / 21 h / 20 °C

2.1: n-butyllithium / tetrahydrofuran; hexane / 2 h / -78 °C

2.2: 81 percent / tetrahydrofuran; hexane / 2 h / -78 °C

3.1: copper(I) iodide / tetrahydrofuran; diethyl ether / 0 °C

3.2: tetrahydrofuran; diethyl ether / 1 h / -78 - -45 °C

3.3: 95 percent / iodine / tetrahydrofuran; diethyl ether / 3 h / -78 - 0 °C

4.1: DIBAL-H / CH₂Cl₂; hexane / 2 h / -78 °C

5.1: 100 percent / imidazole / CH₂Cl₂ / 15 h / 20 °C

6.1: 75 percent / Et₃N / bis(triphenylphosphine)palladium(II) dichloride / 1-methyl-pyrrolidin-2-one / 44 h / 70 °C / 15514.4 Torr

7.1: 66 percent / DIBAL-H / toluene / 1.5 h / -78 °C

With 1H-imidazole; copper(l) iodide; n-butyllithium; sodium hydride; diisobutylaluminium hydride; triethylamine; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; diethyl ether; hexane; dichloromethane; toluene;
DOI:10.1016/S0040-4020(03)00372-7

Reference yield:

: 554416-23-8
5-(4-methoxy-benzyloxy)-pent-2-ynoic acid ethyl ester

: 554416-42-1
2-(tert-butyl-dimethyl-silanyloxymethyl)-5-(4-methoxy-benzyloxy)-3-methyl-pent-2-en-1-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: copper(I) iodide / tetrahydrofuran; diethyl ether / 0 °C

1.2: tetrahydrofuran; diethyl ether / 1 h / -78 - -45 °C

1.3: 95 percent / iodine / tetrahydrofuran; diethyl ether / 3 h / -78 - 0 °C

2.1: DIBAL-H / CH₂Cl₂; hexane / 2 h / -78 °C

3.1: 100 percent / imidazole / CH₂Cl₂ / 15 h / 20 °C

4.1: 75 percent / Et₃N / bis(triphenylphosphine)palladium(II) dichloride / 1-methyl-pyrrolidin-2-one / 44 h / 70 °C / 15514.4 Torr

5.1: 66 percent / DIBAL-H / toluene / 1.5 h / -78 °C

With 1H-imidazole; copper(l) iodide; diisobutylaluminium hydride; triethylamine; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; diethyl ether; hexane; dichloromethane; toluene;
DOI:10.1016/S0040-4020(03)00372-7