(E)-5-(4-methoxybenzyloxy)-3-methylpent-2-en-1-ol

Base Information

• Chemical Name: (E)-5-(4-methoxybenzyloxy)-3-methylpent-2-en-1-ol
• CAS No.: 223457-93-0
• Molecular Formula: C₁₄H₂₀O₃
• Molecular Weight: 236.311
• Mol file: 223457-93-0.mol

Synonyms:(E)-5-(4-methoxybenzyloxy)-3-methylpent-2-en-1-ol

Chemical Property of (E)-5-(4-methoxybenzyloxy)-3-methylpent-2-en-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-5-(4-methoxybenzyloxy)-3-methylpent-2-en-1-ol

There total 2 articles about (E)-5-(4-methoxybenzyloxy)-3-methylpent-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: 54.0%

methyl (E/Z)-5-(4-methoxybenzyloxy)-3-methylpent-2-enoate → (E)-5-(4-methoxybenzyloxy)-3-methylpent-2-en-1-ol (223457-93-0) + (Z)-5-(4-methoxybenzyloxy)-3-methylpent-2-en-1-ol (266675-79-0)

Guidance literature:

With diisobutylaluminium hydride; In hexane; dichloromethane; at -78 ℃; for 1h;

DOI:10.1021/ja071461o

Reference yield: 54.0%

methyl (E/Z)-5-(4-methoxybenzyloxy)-3-methylpent-2-enoate → (E)-5-(4-methoxybenzyloxy)-3-methylpent-2-en-1-ol (223457-93-0)

Guidance literature:

methyl (E/Z)-5-(4-methoxybenzyloxy)-3-methylpent-2-enoate; With diisobutylaluminium hydride; In diethyl ether; hexane; dichloromethane; at -78 - 20 ℃;

With sodium hydroxide; In diethyl ether; hexane; dichloromethane; water; at 20 ℃;

DOI:10.1021/jo901565n

Reference yield:

(E)-5-(4-methoxybenzyloxy)-3-methylpent-2-en-1-ol (223457-93-0) → (S)-1-(4-((1S,2S,3E,5E,7S,8R,10E,12Z,14Z,16S,17S,18E)-17-(tert-butyldimethylsilyloxy)-1-hydroxy-7-methoxy-21-(4-methoxybenzyloxy)-2,6,8,12,14,16,19-heptamethyl-9-oxohenicosa-3,5,10,12,14,18-hexaenyl)thiazol-2-yl)-3-methylbutyl methylcarbamate

Guidance literature:

Multi-step reaction with 14 steps

1.1: 98 percent / MnO₂ / CH₂Cl₂ / 2 h / 20 °C

2.1: chlorodicyclohexylborane; Me₂NEt / diethyl ether; hexane / -78 - 0 °C

2.2: diethyl ether; hexane / 19 h / -78 - -22 °C

3.1: 92 percent / 2,6-lutidine / CH₂Cl₂ / 0.75 h / -78 - -40 °C

4.1: LiBH₄ / tetrahydrofuran / 76 h / -78 - 20 °C

5.1: sodium meta-periodate / methanol; H₂O / 0.67 h / 0 °C

6.1: 18-crown-6; KHMDS / tetrahydrofuran; toluene / 0.25 h / -40 °C

6.2: tetrahydrofuran; toluene / 3 h / -78 °C

7.1: DIBAl-H / CH₂Cl₂; hexane / 1 h / -78 °C

8.1: MnO₂ / CH₂Cl₂ / 20 h / 20 °C

9.1: 18-crown-6; KHMDS / tetrahydrofuran / 0.25 h / -40 °C

9.2: 87 percent / tetrahydrofuran / 6 h / -78 °C

10.1: DIBAl-H / CH₂Cl₂; hexane / 1 h / -78 °C

11.1: Dess-Martin periodinane / CH₂Cl₂ / 1 h / 0 °C

12.1: (c-Hex)2BCl; NEt₃ / diethyl ether / 1 h / 0 °C

12.2: diethyl ether / -78 - -30 °C

12.3: aq. H₂O₂ / diethyl ether; methanol / 1 h / 0 °C / pH 7

13.1: Ac₂O; DMAP / tetrahydrofuran / 0.67 h / 20 °C

13.2: DBU / tetrahydrofuran / 1 h

14.1: NaHCO₃; TBACl; NEt₃ / PdCl₂[PPh₃]2 / dimethylformamide; acetonitrile; H₂O / 0.17 h / 80 °C

With 2,6-dimethylpyridine; dmap; manganese(IV) oxide; sodium periodate; lithium borohydride; 18-crown-6 ether; N,N-dimethyl-ethanamine; dicyclohexylboron chloride; tetrabutyl-ammonium chloride; acetic anhydride; potassium hexamethylsilazane; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; 2.2: Paterson aldol reaction / 6.2: Horner-Wadsworth-Emmons olefination / 9.2: Horner-Wadsworth-Emmons olefination / 12.2: Peterson aldol reaction / 14.1: Heck reaction;

DOI:10.1021/ja071461o

Downstream raw materials:

(2S,4R,5R,E)-5-hydroxy-9-(4-methoxybenzyloxy)-4,7-dimethyl-3-oxonon-6-en-2-yl benzoate

(2S,4R,5R,E)-5-(tert-butyldimethylsilyloxy)-9-(4-methoxybenzyloxy)-4,7-dimethyl-3-oxonon-6-en-2-yl benzoate

(2S,3R,4S,5R,E)-5-(tert-butyldimethylsilyloxy)-9-(4-methoxybenzyloxy)-4,7-dimethylnon-6-ene-2,3-diol

(2R,3R,E)-3-(tert-butyldimethylsilyloxy)-7-(4-methoxybenzyloxy)-2,5-dimethylhept-4-enal