Diethyl 2-(benzyloxy)-2-methylmalonate

Base Information

• Chemical Name: Diethyl 2-(benzyloxy)-2-methylmalonate
• CAS No.: 5774-69-6
• Molecular Formula: C15H20 O5
• Molecular Weight: 280.321
• Hs Code.: 2918990090
• European Community (EC) Number: 227-299-2
• DSSTox Substance ID: DTXSID90973335
• Nikkaji Number: J218.040E
• Wikidata: Q82957225
• Mol file: 5774-69-6.mol

Synonyms:Diethyl 2-(benzyloxy)-2-methylmalonate;5774-69-6;diethyl 2-methyl-2-phenylmethoxypropanedioate;AMY841;DTXSID90973335;AKOS015917673;Diethyl2-(benzyloxy)-2-methylmalonate;Diethyl (benzyloxy)(methyl)propanedioate;FT-0659659;2-(Benzyloxy)-2-methylmalonic acid diethyl ester;1,3-DIETHYL 2-(BENZYLOXY)-2-METHYLPROPANEDIOATE

Chemical Property of Diethyl 2-(benzyloxy)-2-methylmalonate

Chemical Property:

• Appearance/Colour: solid or liquid
• Vapor Pressure: 9.48E-06mmHg at 25°C
• Refractive Index: 1.496
• Boiling Point: 372.6°Cat760mmHg
• Flash Point: 161.9°C
• PSA: 61.83000
• Density: 1.116g/cm³
• LogP: 1.94560
• Solubility.: DCM, Ethyl Acetate, Methanol,
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 280.13107373
• Heavy Atom Count: 20
• Complexity: 302

Purity/Quality:

99% ^*data from raw suppliers

DiethylBenzyloxymethylmalonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(C)(C(=O)OCC)OCC1=CC=CC=C1
• Uses: Diethyl Benzyloxymethylmalonate is an intermediate in the asymmetric synthesis of (R)-(-)-chlozolinate through a chemoenzymatic procedure.

Technology Process of Diethyl 2-(benzyloxy)-2-methylmalonate

There total 2 articles about Diethyl 2-(benzyloxy)-2-methylmalonate 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: 87.0%

diethyl 2-hydroxy-2-methylmalonate (58567-05-8) + benzyl bromide (100-39-0) → diethyl 2-(benzyloxy)-2-methylmalonate (5774-69-6)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 5h;

DOI:10.1016/S0957-4166(01)00040-4

Reference yield:

→ diethyl 2-(benzyloxy)-2-methylmalonate (5774-69-6)

Guidance literature:

α-Brom-α-methyl-malonsaeure-diaethylester, Benzylalkohol / NaH;

Reference yield: 43.0%

diethyl 2-(benzyloxy)-2-methylmalonate (5774-69-6) → C13H18O4

Guidance literature:

With trimethoxysilane; diethylzinc; C₄₈H₄₅NO₅; In hexane; toluene; at 0 ℃; enantioselective reaction; Inert atmosphere; Sealed tube;

DOI:10.1038/s41557-021-00715-0

upstream raw materials:

diethyl 2-hydroxy-2-methylmalonate

benzyl bromide

Downstream raw materials:

(R)-2-benzyloxy-2-methylmalonic acid monoethyl ester

(2S)-2-benzyloxy-3-ethoxy-2-methyl-3-oxo-propanoic acid

(S)-2-benzyloxy-2-methylmalonic acid ethyl phenyl ester

(S)-2-hydroxy-2-methylmalonic acid ethyl phenyl ester

Refernces

• 1、 Barner,Schmid. "Total synthesis of natural α-tocopherol". . p. 2384 - 2399. Retrieved 2007/10/07.