2-[1-benzyloxymethyl-2-bromo-5-(2,2-dimethyl[1,3]dioxolan-4-ylmethyl)-1H-imidazol-4-yl]-2-methylpropionaldehyde

Base Information

Chemical Name:2-[1-benzyloxymethyl-2-bromo-5-(2,2-dimethyl[1,3]dioxolan-4-ylmethyl)-1H-imidazol-4-yl]-2-methylpropionaldehyde
CAS No.:884871-59-4
Molecular Formula:C₂₁H₂₇BrN₂O₄
Molecular Weight:451.36
Hs Code.:

Synonyms:2-[1-benzyloxymethyl-2-bromo-5-(2,2-dimethyl[1,3]dioxolan-4-ylmethyl)-1H-imidazol-4-yl]-2-methylpropionaldehyde

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Chemical Property of 2-[1-benzyloxymethyl-2-bromo-5-(2,2-dimethyl[1,3]dioxolan-4-ylmethyl)-1H-imidazol-4-yl]-2-methylpropionaldehyde

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Technology Process of 2-[1-benzyloxymethyl-2-bromo-5-(2,2-dimethyl[1,3]dioxolan-4-ylmethyl)-1H-imidazol-4-yl]-2-methylpropionaldehyde

There total 8 articles about 2-[1-benzyloxymethyl-2-bromo-5-(2,2-dimethyl[1,3]dioxolan-4-ylmethyl)-1H-imidazol-4-yl]-2-methylpropionaldehyde 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: 98.0%

: 884871-58-3
2-[1-benzyloxymethyl-2-bromo-5-(2,2-dimethyl[1,3]dioxolan-4-ylmethyl)-1H-imidazol-4-yl]-2-methylpropionic acid ethyl ester

: 884871-59-4
2-[1-benzyloxymethyl-2-bromo-5-(2,2-dimethyl[1,3]dioxolan-4-ylmethyl)-1H-imidazol-4-yl]-2-methylpropionaldehyde

Guidance literature:: With diisobutylaluminium hydride; In dichloromethane; at -78 ℃;
DOI:10.1021/jo060084f

Reference yield:

: 3587-60-8
Benzyloxymethyl chloride

: 884871-59-4
2-[1-benzyloxymethyl-2-bromo-5-(2,2-dimethyl[1,3]dioxolan-4-ylmethyl)-1H-imidazol-4-yl]-2-methylpropionaldehyde

Guidance literature:: Multi-step reaction with 7 steps

1.1: triethlyamine / tetrahydrofuran / 1.5 h / 20 °C

1.2: t-BuOK; 18-crown-6 / tetrahydrofuran / 1 h / -78 °C

1.3: 1.89 g / benzyloxymethyl chloride / tetrahydrofuran / 3 h / 70 °C

2.1: 63 percent / benzyltrimethylammonium tribromide; CaCO₃ / CH₂Cl₂; methanol / 4 h / 20 °C

3.1: 80 percent / t-Bu₃P; Pd₂(dba)3; CsF / dioxane; hexane / 100 °C

4.1: 99 percent / N-methylmorpholine N-oxide; osmium tetraoxide / H₂O; acetone / 20 °C

5.1: 74 percent / H₂SO₄ / 48 h

6.1: 95 percent / NBS / tetrahydrofuran / 0 °C

7.1: 98 percent / DIBALH / CH₂Cl₂ / -78 °C

With N-Bromosuccinimide; osmium(VIII) oxide; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; benzyltrimethylammonium tribromide; tri-tert-butyl phosphine; sulfuric acid; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; triethylamine; cesium fluoride; calcium carbonate; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; water; acetone; 3.1: Stille coupling;
DOI:10.1021/jo060084f

Reference yield:

: 28782-45-8
(1H-imidazol-4-yl)-acetic acid ethyl ester

: 884871-59-4
2-[1-benzyloxymethyl-2-bromo-5-(2,2-dimethyl[1,3]dioxolan-4-ylmethyl)-1H-imidazol-4-yl]-2-methylpropionaldehyde

Guidance literature:: Multi-step reaction with 7 steps

1.1: triethlyamine / tetrahydrofuran / 1.5 h / 20 °C

1.2: t-BuOK; 18-crown-6 / tetrahydrofuran / 1 h / -78 °C

1.3: 1.89 g / benzyloxymethyl chloride / tetrahydrofuran / 3 h / 70 °C

2.1: 63 percent / benzyltrimethylammonium tribromide; CaCO₃ / CH₂Cl₂; methanol / 4 h / 20 °C

3.1: 80 percent / t-Bu₃P; Pd₂(dba)3; CsF / dioxane; hexane / 100 °C

4.1: 99 percent / N-methylmorpholine N-oxide; osmium tetraoxide / H₂O; acetone / 20 °C

5.1: 74 percent / H₂SO₄ / 48 h

6.1: 95 percent / NBS / tetrahydrofuran / 0 °C

7.1: 98 percent / DIBALH / CH₂Cl₂ / -78 °C

With N-Bromosuccinimide; osmium(VIII) oxide; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; benzyltrimethylammonium tribromide; tri-tert-butyl phosphine; sulfuric acid; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; triethylamine; cesium fluoride; calcium carbonate; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; water; acetone; 3.1: Stille coupling;
DOI:10.1021/jo060084f