2-benzyl-malonic acid tert-butyl ester methyl ester

Base Information

• Chemical Name: 2-benzyl-malonic acid tert-butyl ester methyl ester
• CAS No.: 4491-46-7
• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.321
• Mol file: 4491-46-7.mol

Synonyms:2-benzyl-malonic acid tert-butyl ester methyl ester

Chemical Property of 2-benzyl-malonic acid tert-butyl ester methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-benzyl-malonic acid tert-butyl ester methyl ester

There total 10 articles about 2-benzyl-malonic acid tert-butyl ester methyl ester 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: 74.0%

methyl t-butyl malonate (42726-73-8) + benzyl bromide (100-39-0) → 2-benzyl-malonic acid tert-butyl ester methyl ester (4491-46-7)

Guidance literature:

methyl t-butyl malonate; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 30h;

benzyl bromide; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 24h;

DOI:10.1021/acs.orglett.6b02682

Reference yield:

2-benzyl-3-(tert-butoxy)-3-oxopropanoic acid (60084-69-7) + diazomethyl-trimethyl-silane (18107-18-1) → benzoic acid methyl ester (93-58-3,5705-52-2,80226-58-0) + 2-benzyl-malonic acid tert-butyl ester methyl ester (4491-46-7) + tert-butyl 3-phenylpropanoate (16537-10-3)

Guidance literature:

In methanol; diethyl ether; at 0 ℃;

DOI:10.1002/cssc.202101963

Reference yield:

mono-tert-butyl malonate (40052-13-9) → 2-benzyl-malonic acid tert-butyl ester methyl ester (4491-46-7)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

2: sodium hydride / tetrahydrofuran; mineral oil / 0 °C / Inert atmosphere

With sodium hydride; triethylamine; In tetrahydrofuran; mineral oil;

DOI:10.1039/c4cc01631a

upstream raw materials:

diazomethane

5-benzyl-2,2-dimethyl-1,3-dioxane-4,6-dione

tert-butyl alcohol

methyl t-butyl malonate

Downstream raw materials:

(S)-1-tert-butyl 3-methyl 2-benzyl-2-fluoromalonate

(R)-1-tert-butyl 3-methyl 2-fluoro-2-benzylmalonate

(5R)-benzyl-N-(3,5-dimethoxybenzyl)-2,4-dioxo-3-[(1R)-1-phenylethyl]-1,3-oxazolidine-5-carboxamide

tert-butyl methyl (R)-2-(benzoyloxy)-2-benzylmalonate

Refernces

• 1、 Odanaka, Yuki,Kanemitsu, Takuya,Iwasaki, Kanako,Mochizuki, Yukiko,Miyazaki, Michiko,Nagata, Kazuhiro,Kato, Masaru,Itoh, Takashi. "Asymmetric Michael addition of malonic diesters to acrylates by phase-transfer catalysis toward the construction of quaternary stereogenic α-carbons". supporting information. p. 209 - 219. Retrieved 2018/12/11.
• 2、 -. "FACTOR XIa INHIBITORS". Page/Page column 80; 82. . Retrieved 2015/12/09.