(E)-2-isopropyl-3-methyl-3-hydroxy-4-<(methoxymethyl)oxy>-1-(4,5-diphenyloxazol-2-yl)-1,4,5-hexatriene

Base Information

• Chemical Name: (E)-2-isopropyl-3-methyl-3-hydroxy-4-<(methoxymethyl)oxy>-1-(4,5-diphenyloxazol-2-yl)-1,4,5-hexatriene
• CAS No.: 124771-33-1
• Molecular Formula: C₂₇H₂₉NO₄
• Molecular Weight: 431.532

Synonyms:(E)-2-isopropyl-3-methyl-3-hydroxy-4-<(methoxymethyl)oxy>-1-(4,5-diphenyloxazol-2-yl)-1,4,5-hexatriene

Chemical Property of (E)-2-isopropyl-3-methyl-3-hydroxy-4-<(methoxymethyl)oxy>-1-(4,5-diphenyloxazol-2-yl)-1,4,5-hexatriene

Chemical Property:

Purity/Quality:

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Technology Process of (E)-2-isopropyl-3-methyl-3-hydroxy-4-<(methoxymethyl)oxy>-1-(4,5-diphenyloxazol-2-yl)-1,4,5-hexatriene

There total 10 articles about (E)-2-isopropyl-3-methyl-3-hydroxy-4-<(methoxymethyl)oxy>-1-(4,5-diphenyloxazol-2-yl)-1,4,5-hexatriene 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%

1-lithio-1-(methoxymethoxy)allene + (E)-3-isopropyl-4-(4,5-diphenyloxazol-2-yl)but-3-en-2-one (102368-35-4) → (E)-2-isopropyl-3-methyl-3-hydroxy-4-<(methoxymethyl)oxy>-1-(4,5-diphenyloxazol-2-yl)-1,4,5-hexatriene (124771-33-1)

Guidance literature:

In tetrahydrofuran; diethyl ether; at -78 ℃;

DOI:10.1016/S0040-4039(01)80391-9

Reference yield:

(E)-4-methyl-2-(triethylsilyloxy)pent-2-ene (57137-74-3) → (E)-2-isopropyl-3-methyl-3-hydroxy-4-<(methoxymethyl)oxy>-1-(4,5-diphenyloxazol-2-yl)-1,4,5-hexatriene (124771-33-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 2.) DBU, molecular sieves (3 Angstroem) / 1.) TMSOTf / 1.) CH₂Cl₂, -78 deg C, 8 h; 2.) CH₂Cl₂, reflux, 4 h

2: 1.) n-BuLi / 1.) ether, THF, -78 deg C, 30 min; 2.) ether, THF, -78 deg C, 5 min

With n-butyllithium; 3 A molecular sieve; 1,8-diazabicyclo[5.4.0]undec-7-ene; trimethylsilyl trifluoromethanesulfonate;

DOI:10.1021/ja00272a045

Reference yield:

2-Dimethoxymethyl-4,5-diphenyl-oxazole (102368-47-8) → (E)-2-isopropyl-3-methyl-3-hydroxy-4-<(methoxymethyl)oxy>-1-(4,5-diphenyloxazol-2-yl)-1,4,5-hexatriene (124771-33-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 2.) DBU, molecular sieves (3 Angstroem) / 1.) TMSOTf / 1.) CH₂Cl₂, -78 deg C, 8 h; 2.) CH₂Cl₂, reflux, 4 h

2: 1.) n-BuLi / 1.) ether, THF, -78 deg C, 30 min; 2.) ether, THF, -78 deg C, 5 min

With n-butyllithium; 3 A molecular sieve; 1,8-diazabicyclo[5.4.0]undec-7-ene; trimethylsilyl trifluoromethanesulfonate;

DOI:10.1021/ja00272a045

upstream raw materials:

1-(methoxymethoxy)-1,2-propadiene

(E)-3-isopropyl-4-(4,5-diphenyloxazol-2-yl)but-3-en-2-one

(E)-4-methyl-2-(triethylsilyloxy)pent-2-ene

2-Dimethoxymethyl-4,5-diphenyl-oxazole

Downstream raw materials:

4-(4,5-Diphenyl-oxazol-2-yl)-3-isopropyl-2-methyl-5-methylene-cyclopent-2-enone

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