methyl 2-methyl-3-oxopentanoate

Base Information

• Chemical Name: methyl 2-methyl-3-oxopentanoate
• CAS No.: 17422-12-7
• Molecular Formula: C7H12O3
• Molecular Weight: 144.17
• Hs Code.: 2918300090
• Mol file: 17422-12-7.mol

Synonyms:methyl 2-propionylpropionate;methyl 2-methyl-3-ketovalerate;2-Methyl-3-oxopentansaeure-methylester;Pentanoic acid,2-methyl-3-oxo-,methyl ester;2-Methyl-3-oxopentanoic acid methyl ester;

Chemical Property of methyl 2-methyl-3-oxopentanoate

Chemical Property:

• Vapor Pressure: 0.686mmHg at 25°C
• Boiling Point: 185.8oC at 760 mmHg
• Flash Point: 68.9oC
• PSA: 43.37000
• Density: 0.993g/cm3
• LogP: 0.77460
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)

Purity/Quality:

98%min ^*data from raw suppliers

2-METHYL-3-OXO-PENTANOIC ACID METHYL ESTER ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: 2-Methyl-3-oxopentanoic Acid Methyl Ester is an intermediate in the synthesis of antiproliferative polyketide (+)-R-aureothin.

Technology Process of methyl 2-methyl-3-oxopentanoate

There total 11 articles about methyl 2-methyl-3-oxopentanoate 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: 96.0%

methyl propanoyl acetate (30414-53-0) + methyl iodide (74-88-4) → methyl 2-methyl-3-oxopentanoate (17422-12-7)

Guidance literature:

With potassium carbonate; In acetone; for 12h; Inert atmosphere; Reflux;

DOI:10.1016/j.tet.2016.11.064

Reference yield: 87.0%

propanoic acid methyl ester (554-12-1) → methyl 2-methyl-3-oxopentanoate (17422-12-7)

Guidance literature:

With sodium hydride; In methanol; paraffin; benzene; for 7h; Heating;

Reference yield: 73.0%

propanoic acid methyl ester (554-12-1) + isopentanoyl chloride (108-12-3) → methyl 2-methyl-3-oxopentanoate (17422-12-7) + methyl 2,5-dimethyl-3-oxohexanoate (172659-42-6)

Guidance literature:

propanoic acid methyl ester; isopentanoyl chloride; With 1,2-dimethyl-1H-imidazole; In dichloromethane; at -45 ℃; for 0.166667h;

With tributyl-amine; titanium tetrachloride; In dichloromethane; at -45 ℃; for 0.5h;

DOI:10.1021/ja043833o

upstream raw materials:

propanoic acid methyl ester

2-bromo-2-methylpropionic acid methyl ester

Methyl 2-bromopropionate

methanol

Downstream raw materials:

2,2-dimethyl-3-oxo-valeric acid methyl ester

(+/-)-methyl 1,3-dimethyl-2-oxo-3-cyclohexene-1-carboxylate

1'-ethylpropyl-2-methyl-3-oxopentanoate

6-ethyl-5-methyl-2-phenyl-4(3H)-pyrimidinone

Refernces

• 1、 Johnson,Shiner. "". . p. 1350,1354. Retrieved 1953.
• 2、 Sung,Wu. "Convenient and efficient syntheses of β-keto esters and β-keto amides directly from α-alkylacetyl chlorides". . p. 3069 - 3074. Retrieved 2001.
• 3、 Huynh, Uyen,McDonald, Stacey L.,Lim, Daniel,Uddin, Md. Nasir,Wengryniuk, Sarah E.,Dey, Sumit,Coltart, Don M.. "Formation, Alkylation, and Hydrolysis of Chiral Nonracemic N-Amino Cyclic Carbamate Hydrazones: An Approach to the Enantioselective α-Alkylation of Ketones". . p. 12951 - 12964. Retrieved 2018/11/30.
• 4、 Huynh, Uyen,Uddin, Md. Nasir,Wengryniuk, Sarah E.,McDonald, Stacey L.,Coltart, Don M.. "On the regioselectivity and diastereoselectivity of ACC hydrazone alkylation". supporting information. p. 432 - 436. Retrieved 2017/01/13.