ethyl (E)-5-(p-methoxybenzyloxy)-2-iodo-3-methylpent-2-enoate

Base Information

• Chemical Name: ethyl (E)-5-(p-methoxybenzyloxy)-2-iodo-3-methylpent-2-enoate
• CAS No.: 554416-24-9
• Molecular Formula: C₁₆H₂₁IO₄
• Molecular Weight: 404.245
• Mol file: 554416-24-9.mol

Synonyms:ethyl (E)-5-(p-methoxybenzyloxy)-2-iodo-3-methylpent-2-enoate

Chemical Property of ethyl (E)-5-(p-methoxybenzyloxy)-2-iodo-3-methylpent-2-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (E)-5-(p-methoxybenzyloxy)-2-iodo-3-methylpent-2-enoate

There total 1 articles about ethyl (E)-5-(p-methoxybenzyloxy)-2-iodo-3-methylpent-2-enoate 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: 95.0%

methyllithium (917-54-4) + 5-(4-methoxy-benzyloxy)-pent-2-ynoic acid ethyl ester (554416-23-8) → ethyl (E)-5-(p-methoxybenzyloxy)-2-iodo-3-methylpent-2-enoate (554416-24-9)

Guidance literature:

methyllithium; With copper(l) iodide; In tetrahydrofuran; diethyl ether; at 0 ℃;

5-(4-methoxy-benzyloxy)-pent-2-ynoic acid ethyl ester; In tetrahydrofuran; diethyl ether; at -78 - -45 ℃; for 1h;

With iodine; In tetrahydrofuran; diethyl ether; at -78 - 0 ℃; for 3h;

DOI:10.1016/S0040-4020(03)00372-7

Reference yield:

ethyl (E)-5-(p-methoxybenzyloxy)-2-iodo-3-methylpent-2-enoate (554416-24-9) → tert-Butyl-{(Z)-2-chloromethyl-5-[(4R,5R)-5-((E)-2-iodo-vinyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-3-methyl-pent-2-enyloxy}-diphenyl-silane

Guidance literature:

Multi-step reaction with 16 steps

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

2.1: 100 percent / imidazole / CH₂Cl₂ / 15 h / 20 °C

3.1: 75 percent / Et₃N / bis(triphenylphosphine)palladium(II) dichloride / 1-methyl-pyrrolidin-2-one / 44 h / 70 °C / 15514.4 Torr

4.1: 66 percent / DIBAL-H / toluene / 1.5 h / -78 °C

5.1: 100 percent / imidazole / CH₂Cl₂ / 0 - 20 °C

6.1: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 1.08 h / 20 °C

7.1: triethylamine / CH₂Cl₂ / 1.5 h / 0 °C

8.1: 5.09 g / sodium iodide / acetone / 2.5 h / Heating

9.1: t-butyllithium / tetrahydrofuran; pentane / 2 h / -78 °C

9.2: 62 percent / tetrahydrofuran; pentane / 16 h / -100 - -78 °C

10.1: 90 percent / aqueous oxalic acid / diethyl ether / 2.5 h / 20 °C

11.1: diethyl cyanophosphonate / tetrahydrofuran / 1 h / 20 °C

11.2: samarium; diiodoethane; methanol / tetrahydrofuran / 2 h / 23 °C

12.1: 89 percent / DIBAL-H / toluene / 1.5 h / -78 °C

13.1: potassium hydride / tetrahydrofuran / 0.08 h / 0 °C

13.2: tetrahydrofuran / 2.5 h / -16 - 0 °C

14.1: chromium dichloride / dioxane; tetrahydrofuran / 3 h / 20 °C

15.1: 524 mg / PPTS; water / ethanol / 15 h / 20 °C

16.1: 97 percent / triphenylphosphine; hexachloroacetone / tetrahydrofuran / 0.5 h / -40 °C

With 1H-imidazole; chromium dichloride; 1,1,1,3,3,3-hexachloro-propan-2-one; diethyl cyanophosphonate; water; tert.-butyl lithium; pyridinium p-toluenesulfonate; oxalic acid; potassium hydride; diisobutylaluminium hydride; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium iodide; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; 1,4-dioxane; 1-methyl-pyrrolidin-2-one; diethyl ether; ethanol; hexane; dichloromethane; water; acetone; toluene; pentane; 14.1: Takai homologation;

DOI:10.1016/S0040-4020(03)00372-7

Reference yield:

ethyl (E)-5-(p-methoxybenzyloxy)-2-iodo-3-methylpent-2-enoate (554416-24-9) → (E)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-[(4R,5R)-5-((E)-2-iodo-vinyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-3-methyl-pent-2-en-1-ol (554416-35-2)

Guidance literature:

Multi-step reaction with 15 steps

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

2.1: 100 percent / imidazole / CH₂Cl₂ / 15 h / 20 °C

3.1: 75 percent / Et₃N / bis(triphenylphosphine)palladium(II) dichloride / 1-methyl-pyrrolidin-2-one / 44 h / 70 °C / 15514.4 Torr

4.1: 66 percent / DIBAL-H / toluene / 1.5 h / -78 °C

5.1: 100 percent / imidazole / CH₂Cl₂ / 0 - 20 °C

6.1: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 1.08 h / 20 °C

7.1: triethylamine / CH₂Cl₂ / 1.5 h / 0 °C

8.1: 5.09 g / sodium iodide / acetone / 2.5 h / Heating

9.1: t-butyllithium / tetrahydrofuran; pentane / 2 h / -78 °C

9.2: 62 percent / tetrahydrofuran; pentane / 16 h / -100 - -78 °C

10.1: 90 percent / aqueous oxalic acid / diethyl ether / 2.5 h / 20 °C

11.1: diethyl cyanophosphonate / tetrahydrofuran / 1 h / 20 °C

11.2: samarium; diiodoethane; methanol / tetrahydrofuran / 2 h / 23 °C

12.1: 89 percent / DIBAL-H / toluene / 1.5 h / -78 °C

13.1: potassium hydride / tetrahydrofuran / 0.08 h / 0 °C

13.2: tetrahydrofuran / 2.5 h / -16 - 0 °C

14.1: chromium dichloride / dioxane; tetrahydrofuran / 3 h / 20 °C

15.1: 524 mg / PPTS; water / ethanol / 15 h / 20 °C

With 1H-imidazole; chromium dichloride; diethyl cyanophosphonate; water; tert.-butyl lithium; pyridinium p-toluenesulfonate; oxalic acid; potassium hydride; diisobutylaluminium hydride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium iodide; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; 1,4-dioxane; 1-methyl-pyrrolidin-2-one; diethyl ether; ethanol; hexane; dichloromethane; water; acetone; toluene; pentane; 14.1: Takai homologation;

DOI:10.1016/S0040-4020(03)00372-7

upstream raw materials:

methyllithium

5-(4-methoxy-benzyloxy)-pent-2-ynoic acid ethyl ester

Downstream raw materials:

(E)-2-Iodo-5-(4-methoxy-benzyloxy)-3-methyl-pent-2-en-1-ol

(E)-5-(p-methoxybenzyloxy)-1-(tert-butyldimethylsilyloxy)-2-iodo-3-methylpent-2-ene

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

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