tert-butyl 2-(2-(1,3-dioxolan-2-yl)phenyl)-2-cyanopropanoate

Base Information

• Chemical Name: tert-butyl 2-(2-(1,3-dioxolan-2-yl)phenyl)-2-cyanopropanoate
• CAS No.: 1491842-34-2
• Molecular Formula: C₁₇H₂₁NO₄
• Molecular Weight: 303.358
• Mol file: 1491842-34-2.mol

Synonyms:tert-butyl 2-(2-(1,3-dioxolan-2-yl)phenyl)-2-cyanopropanoate

Chemical Property of tert-butyl 2-(2-(1,3-dioxolan-2-yl)phenyl)-2-cyanopropanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl 2-(2-(1,3-dioxolan-2-yl)phenyl)-2-cyanopropanoate

There total 4 articles about tert-butyl 2-(2-(1,3-dioxolan-2-yl)phenyl)-2-cyanopropanoate 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: 85.0%

2-(2-bromophenyl)-1,3-dioxolan (34824-58-3) + cyanoacetic acid tert-butyl ester (1116-98-9) + methyl iodide (74-88-4) → tert-butyl 2-(2-(1,3-dioxolan-2-yl)phenyl)-2-cyanopropanoate (1491842-34-2)

Guidance literature:

2-(2-bromophenyl)-1,3-dioxolan; cyanoacetic acid tert-butyl ester; With dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); sodium t-butanolate; In 1,4-dioxane; at 70 ℃; for 4h;

methyl iodide; at 70 ℃; for 8h;

DOI:10.1039/c5ob02320c

Reference yield:

tert-butyl 2-(2-(1,3-dioxolan-2-yl)phenyl)-2-cyanoacetate + methyl iodide (74-88-4) → tert-butyl 2-(2-(1,3-dioxolan-2-yl)phenyl)-2-cyanopropanoate (1491842-34-2)

Guidance literature:

With sodium t-butanolate; In 1,4-dioxane; at 70 ℃; for 8h; Inert atmosphere;

DOI:10.1021/ol4030309

Reference yield:

ortho-bromobenzaldehyde (6630-33-7) → tert-butyl 2-(2-(1,3-dioxolan-2-yl)phenyl)-2-cyanopropanoate (1491842-34-2)

Guidance literature:

Multi-step reaction with 3 steps

1: toluene-4-sulfonic acid / toluene / 18 h / Dean-Stark; Reflux

2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium t-butanolate / 1,4-dioxane / 4 h / 70 °C / Inert atmosphere

3: sodium t-butanolate / 1,4-dioxane / 8 h / 70 °C / Inert atmosphere

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; toluene-4-sulfonic acid; sodium t-butanolate; In 1,4-dioxane; toluene;

DOI:10.1021/ol4030309

upstream raw materials:

methyl iodide

ortho-bromobenzaldehyde

2-(2-bromophenyl)-1,3-dioxolan

cyanoacetic acid tert-butyl ester

Downstream raw materials:

3-amino-4-methylisoquinoline

Refernces

• 1、 Pilgrim, Ben S.,Gatland, Alice E.,McTernan, Charlie T.,Procopiou, Panayiotis A.,Donohoe, Timothy J.. "Modular isoquinoline synthesis using catalytic enolate arylation and in situ functionalization". supporting information. p. 6190 - 6193. Retrieved 2014/01/17.