4-(hex-3-ene-1,5-diynyl)-2-hydroxymethyl-4-<(tert-butyldimethylsilyl)oxy>-cyclohex-1-ene

Base Information

Chemical Name:4-(hex-3-ene-1,5-diynyl)-2-hydroxymethyl-4-<(tert-butyldimethylsilyl)oxy>-cyclohex-1-ene
CAS No.:156826-24-3
Molecular Formula:C₁₉H₂₈O₂Si
Molecular Weight:316.516
Hs Code.:

Synonyms:4-(hex-3-ene-1,5-diynyl)-2-hydroxymethyl-4-<(tert-butyldimethylsilyl)oxy>-cyclohex-1-ene

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Chemical Property of 4-(hex-3-ene-1,5-diynyl)-2-hydroxymethyl-4-<(tert-butyldimethylsilyl)oxy>-cyclohex-1-ene

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Technology Process of 4-(hex-3-ene-1,5-diynyl)-2-hydroxymethyl-4-<(tert-butyldimethylsilyl)oxy>-cyclohex-1-ene

There total 7 articles about 4-(hex-3-ene-1,5-diynyl)-2-hydroxymethyl-4-<(tert-butyldimethylsilyl)oxy>-cyclohex-1-ene 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: 86.0%

: 156826-23-2
2-hydroxymethyl-4-<(tert-butyldimethylsilyl)oxy>-4-(6-trimethylsilanyl-hex-3-ene-1,5-diynyl)-cyclohex-1-ene

: 156826-24-3
4-(hex-3-ene-1,5-diynyl)-2-hydroxymethyl-4-<(tert-butyldimethylsilyl)oxy>-cyclohex-1-ene

Guidance literature:: With potassium carbonate; In methanol; at 25 ℃; for 2.8h;
DOI:10.1016/S0040-4020(01)80632-3

Reference yield:

: 66838-90-2
5-Oxo-1-cyclohexenecarboxylic acid methyl ester

: 156826-24-3
4-(hex-3-ene-1,5-diynyl)-2-hydroxymethyl-4-<(tert-butyldimethylsilyl)oxy>-cyclohex-1-ene

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) 1.0 M lithium bistrimethylsilylamide, 2.) cerium trichloride / 1.) tetrahydrofuran, -78 deg C, 30 min, 2.) tetrahydrofuran, -78 deg C, 5 min, 3.) tetrahydrofuran, -78 deg C, 20 min

2: 97 percent / 2,6-lutidine / CH₂Cl₂ / 5 h

3: 100 percent / 1.0M diisobutylaluminumhydride in hexane / CH₂Cl₂ / 0.17 h / -78 °C

4: 99 percent / potassium carbonate / methanol / 16 h / 25 °C

5: 96 percent / n-butylamine, CuI, Pd(PPh₃)4 / tetrahydrofuran / 2.23 h / 25 °C

6: 86 percent / potassium carbonate / methanol / 2.8 h / 25 °C

With 2,6-dimethylpyridine; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; cerium(III) chloride; diisobutylaluminium hydride; potassium carbonate; N-butylamine; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1016/S0040-4020(01)80632-3

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 156826-24-3
4-(hex-3-ene-1,5-diynyl)-2-hydroxymethyl-4-<(tert-butyldimethylsilyl)oxy>-cyclohex-1-ene

Guidance literature:: Multi-step reaction with 5 steps

1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 5 h

2: 100 percent / 1.0M diisobutylaluminumhydride in hexane / CH₂Cl₂ / 0.17 h / -78 °C

3: 99 percent / potassium carbonate / methanol / 16 h / 25 °C

4: 96 percent / n-butylamine, CuI, Pd(PPh₃)4 / tetrahydrofuran / 2.23 h / 25 °C

5: 86 percent / potassium carbonate / methanol / 2.8 h / 25 °C

With 2,6-dimethylpyridine; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; diisobutylaluminium hydride; potassium carbonate; N-butylamine; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1016/S0040-4020(01)80632-3