ethyl 3-(2,5,5-trimethyl-1,3-dioxan-2-yl)propanoate

Base Information

• Chemical Name: ethyl 3-(2,5,5-trimethyl-1,3-dioxan-2-yl)propanoate
• CAS No.: 16837-24-4
• Molecular Formula: C12H22 O4
• Molecular Weight: 230.3007
• Mol file: 16837-24-4.mol

Synonyms:m-Dioxane-2-propionicacid, 2,5,5-trimethyl-, ethyl ester (8CI); NSC 55201

Chemical Property of ethyl 3-(2,5,5-trimethyl-1,3-dioxan-2-yl)propanoate

Chemical Property:

• Vapor Pressure: 0.00656mmHg at 25°C
• Boiling Point: 271.2°Cat760mmHg
• Flash Point: 111.4°C
• Density: 0.976g/cm³

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of ethyl 3-(2,5,5-trimethyl-1,3-dioxan-2-yl)propanoate

There total 2 articles about ethyl 3-(2,5,5-trimethyl-1,3-dioxan-2-yl)propanoate 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: 98.0%

4-oxopentanoic acid ethyl ester (539-88-8) + 2,2-Dimethyl-1,3-propanediol (126-30-7) → 3-(2,5,5-trimethyl-[1,3]dioxan-2-yl)-propionic acid ethyl ester (16837-24-4)

Guidance literature:

With toluene-4-sulfonic acid; orthoformic acid triethyl ester; In dichloromethane; at 20 ℃; for 19h; Inert atmosphere;

DOI:10.1021/acs.orglett.8b01987

Reference yield:

→ 3-(2,5,5-trimethyl-[1,3]dioxan-2-yl)-propionic acid ethyl ester (16837-24-4)

Guidance literature:

entspr. Diol, entspr. Keton;

DOI:10.1021/ja00990a039

Reference yield:

3-(2,5,5-trimethyl-[1,3]dioxan-2-yl)-propionic acid ethyl ester (16837-24-4) → N-benzyl-6-aza-artemisinin

Guidance literature:

Multi-step reaction with 10 steps

1.1: diisobutylaluminium hydride / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

2.1: (S)-4-[2-(diphenylphosphine)-1-naphthalene]-N-[(R)-1-phenethyl]-1-phthalazine; copper(I) bromide; carbonic acid dimethyl ester / 14 h / 20 °C / Molecular sieve; Inert atmosphere

3.1: di-isopropyl ether; titanium(IV) isopropylate; isopropylmagnesium chloride / diethyl ether / 4.58 h / -78 - -40 °C / Inert atmosphere

3.2: 0.33 h / -40 °C / Inert atmosphere

4.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 - 20 °C / Inert atmosphere

4.2: 3 h / 0 - 20 °C / Inert atmosphere

5.1: n-butyllithium; diethylamine / tetrahydrofuran; hexane / -78 - -10 °C / Inert atmosphere

6.1: dichloromethane; water / 1.5 h / 0 - 20 °C / Inert atmosphere

7.1: ozone / dichloromethane / 0.5 h / -78 °C

8.1: trifluoroacetic acid / 12 h / -78 - 20 °C / Inert atmosphere

9.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; aq. phosphate buffer / 4.5 h / 20 °C / pH 11 / Inert atmosphere

10.1: C₅H₁₀BO₅^(1-)*Na⁽¹⁺⁾; acetic acid / 1,2-dichloro-ethane / 12 h / 38 °C / Inert atmosphere

With titanium(IV) isopropylate; n-butyllithium; (S)-4-[2-(diphenylphosphine)-1-naphthalene]-N-[(R)-1-phenethyl]-1-phthalazine; di-isopropyl ether; C₅H₁₀BO₅^(1-)*Na⁽¹⁺⁾; isopropylmagnesium chloride; diisobutylaluminium hydride; ozone; acetic acid; diethylamine; diisopropylamine; carbonic acid dimethyl ester; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; copper(I) bromide; In tetrahydrofuran; aq. phosphate buffer; diethyl ether; hexane; dichloromethane; water; 1,2-dichloro-ethane;

DOI:10.1021/acs.orglett.8b01987

upstream raw materials:

4-oxopentanoic acid ethyl ester

2,2-Dimethyl-1,3-propanediol

Refernces

• 1、 Bonepally, Karunakar Reddy,Hiruma, Takahisa,Mizoguchi, Haruki,Ochiai, Kyohei,Suzuki, Shun,Oikawa, Hideaki,Ishiyama, Aki,Hokari, Rei,Iwatsuki, Masato,Otoguro, Kazuhiko,Omura, Satoshi,Oguri, Hiroki. "Design and de Novo Synthesis of 6-Aza-artemisinins". . p. 4667 - 4671. Retrieved 2018.
• 2、 Bonepally, Karunakar Reddy,Hiruma, Takahisa,Hokari, Rei,Ishiyama, Aki,Iwatsuki, Masato,Kato, Nobutaka,Koi, Hikari,Matsuoka, Naoya,Mizoguchi, Haruki,Mura, Satoshi,Ochiai, Kyohei,Oguri, Hiroki,Oikawa, Hideaki,Otoguro, Kazuhiko,Suzuki, Shun,Takahashi, Norihito,Yamagishi, Yutaka. "Rapid and Systematic Exploration of Chemical Space Relevant to Artemisinins: Anti-malarial Activities of Skeletally Diversified Tetracyclic Peroxides and 6-Aza-artemisinins". . p. 9694 - 9712. Retrieved 2020.