Ethyl 4,4-dimethoxy-3-methyl-2-butenoate

Base Information

• Chemical Name: Ethyl 4,4-dimethoxy-3-methyl-2-butenoate
• CAS No.: 83803-81-0
• Molecular Formula: C9H16 O4
• Molecular Weight: 188.224
• European Community (EC) Number: 280-901-5
• Nikkaji Number: J296.266G,J3.531.585C
• Mol file: 83803-81-0.mol

Synonyms:Ethyl 4,4-dimethoxy-3-methyl-2-butenoate;83803-81-0;EINECS 280-901-5;SCHEMBL2890685;J3.531.585C;4,4-Dimethoxy-3-methyl-2-butenoic acid ethyl ester;(E)-4,4-Dimethoxy-3-methyl-2-butenoic acid ethyl ester

Chemical Property of Ethyl 4,4-dimethoxy-3-methyl-2-butenoate

Chemical Property:

• Vapor Pressure: 0.0381mmHg at 25°C
• Boiling Point: 240.4°C at 760 mmHg
• Flash Point: 97.5°C
• Density: 1.006g/cm³
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 188.10485899
• Heavy Atom Count: 13
• Complexity: 182

Purity/Quality:

99.9% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C=C(C)C(OC)OC
• Isomeric SMILES: CCOC(=O)/C=C(\C)/C(OC)OC

Technology Process of Ethyl 4,4-dimethoxy-3-methyl-2-butenoate

There total 2 articles about Ethyl 4,4-dimethoxy-3-methyl-2-butenoate 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: 95.0%

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + Pyruvic aldehyde dimethyl acetal (6342-56-9) → ethyl (E/Z)-4,4-dimethoxy-3-methylbut-2-enoate (83803-81-0)

Guidance literature:

With tetrahydrofuran; sodium hydride;

DOI:10.1016/S0040-4039(00)80056-8

Reference yield:

Pyruvic aldehyde dimethyl acetal (6342-56-9) + ethyl 2-(diethoxyphosphoryl)acetate lithium salt (90208-14-3) → ethyl (E/Z)-4,4-dimethoxy-3-methylbut-2-enoate (83803-81-0)

Guidance literature:

Product distribution; other solvents, other counter ion, other phosphonoesters;

DOI:10.1016/S0040-4039(01)90386-7

Reference yield: 100.0%

ethyl (E/Z)-4,4-dimethoxy-3-methylbut-2-enoate (83803-81-0) → 5-hydroxy-4-methyl-5H-furan-2-one (40834-42-2)

Guidance literature:

With hydrogenchloride; iodine; for 3h; Heating;

DOI:10.1248/cpb.55.1365

upstream raw materials:

diethoxyphosphoryl-acetic acid ethyl ester

Pyruvic aldehyde dimethyl acetal

ethyl 2-(diethoxyphosphoryl)acetate lithium salt

Downstream raw materials:

ethyl (E)-3-formyl-2-butenoate

5-methylpyridazin-3(2H)-one

3-methoxy-estra-1,3,5⁽¹⁰⁾,8⁽⁹⁾,14⁽¹⁵⁾-pentaene-17-one

(S)-benzyloxy-1-ethoxymethoxy-2-methylbutane

Refernces

• 1、 -. "Process for total synthesis of pladienolide B and pladienolide D". Page/Page column 27-28. . Retrieved 2010/11/29.
• 2、 Hu, Qi-Ying,Rege, Pankaj D.,Corey. "Simple, Catalytic Enantioselective Syntheses of Estrone and Desogestrel". . p. 5984 - 5986. Retrieved 2007/10/03.