diethyl methyl(naphthalen-1-ylmethyl)propanedioate

Base Information

• Chemical Name: diethyl methyl(naphthalen-1-ylmethyl)propanedioate
• CAS No.: 4512-62-3
• Molecular Formula: C₁₉H₂₂O₄
• Molecular Weight: 314.381
• Mol file: 4512-62-3.mol

Synonyms:Malonicacid, methyl(1-naphthylmethyl)-, diethyl ester (7CI,8CI); NSC 59947

Chemical Property of diethyl methyl(naphthalen-1-ylmethyl)propanedioate

Chemical Property:

• Vapor Pressure: 2.21E-07mmHg at 25°C
• Boiling Point: 423.6°Cat760mmHg
• Flash Point: 207.2°C
• Density: 1.127g/cm³

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of diethyl methyl(naphthalen-1-ylmethyl)propanedioate

There total 7 articles about diethyl methyl(naphthalen-1-ylmethyl)propanedioate 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: 92.0%

Diethyl methylmalonate (609-08-5) + methyl (naphthalen-1-ylmethyl) carbonate → diethyl methyl[(1-naphthyl)methyl]malonate (4512-62-3)

Guidance literature:

With 1,1'-bis-(diphenylphosphino)ferrocene; N,O-bis-(trimethylsilyl)-acetamide; {(η4-1,5-cyclooctadiene)Pd(η3-allyl)}BF4; potassium acetate; In tetrahydrofuran; at 80 ℃; for 1h;

DOI:10.1021/ja037735z

Reference yield: 74.0%

naphthalen-1-ylmethyl 2,3,4,5,6-pentafluorobenzoate + Diethyl methylmalonate (609-08-5) → diethyl methyl[(1-naphthyl)methyl]malonate (4512-62-3)

Guidance literature:

With 1,1'-bis-(diphenylphosphino)ferrocene; bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; In toluene; at 80 ℃; for 18h; Glovebox;

DOI:10.1021/acs.orglett.9b03475

Reference yield:

1-naphthalene methanol (4780-79-4) → diethyl methyl[(1-naphthyl)methyl]malonate (4512-62-3)

Guidance literature:

Multi-step reaction with 2 steps

1: dmap; triethylamine / 17 h / 0 - 20 °C / Inert atmosphere

2: 1,1'-bis-(diphenylphosphino)ferrocene; bis(1,5-cyclooctadiene)nickel ⁽⁰⁾ / toluene / 18 h / 80 °C / Glovebox

With dmap; 1,1'-bis-(diphenylphosphino)ferrocene; bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; triethylamine; In toluene;

DOI:10.1021/acs.orglett.9b03475

upstream raw materials:

sodium diethyl methylmalonate

1-Chloromethylnaphthalene

2-(bromomethyl)naphthalene

Diethyl methylmalonate

Downstream raw materials:

Methyl-<1-naphthyl-methyl>-malonsaeure

Refernces

• 1、 Kuwano, Ryoichi,Kondo, Yutaka. "Palladium-catalyzed benzylation of active methine compounds without additional base: Remarkable effect of 1,5-cyclooctadiene". . p. 3545 - 3547. Retrieved 2007/10/03.