Propanedioic acid, (1-hydroxyethylidene)-, dimethyl ester

Base Information

• Chemical Name: Propanedioic acid, (1-hydroxyethylidene)-, dimethyl ester
• CAS No.: 113934-48-8
• Molecular Formula: C7H10O5
• Mol file: 113934-48-8.mol

Synonyms:

Chemical Property of Propanedioic acid, (1-hydroxyethylidene)-, dimethyl ester

Chemical Property:

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Propanedioic acid, (1-hydroxyethylidene)-, dimethyl ester

There total 1 articles about Propanedioic acid, (1-hydroxyethylidene)-, dimethyl ester 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:

acetyl chloride (75-36-5) + malonic acid dimethyl ester (108-59-8) → dimethyl acetylmalonate (17094-36-9) + 2-(1-Hydroxy-ethylidene)-malonic acid dimethyl ester (113934-48-8)

Guidance literature:

With triethylamine; magnesium chloride; In acetonitrile; at 0 - 25 ℃; for 23h; Overall yield = 96 %; Overall yield = 44.3 g; Inert atmosphere;

DOI:10.1021/ja506472u

Reference yield:

2-(1-Hydroxy-ethylidene)-malonic acid dimethyl ester (113934-48-8) → C46H51NO11Si

Guidance literature:

Multi-step reaction with 7 steps

1.1: potassium carbonate / N,N-dimethyl-formamide / 17 h / 0 - 25 °C / Inert atmosphere

2.1: sodium methylate; hydroxylamine hydrochloride / methanol / 24 h / 0 - 25 °C / Inert atmosphere

3.1: silver(l) oxide / N,N-dimethyl-formamide / 18 h / 25 °C / Inert atmosphere; Darkness

4.1: sodium hydroxide / ethanol; water / 3 h / 25 °C / Inert atmosphere

5.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 3 h / Inert atmosphere; Reflux

6.1: lithium hexamethyldisilazane / tetrahydrofuran; ethylbenzene / 0.5 h / -78 °C / Inert atmosphere

6.2: 2 h / -78 °C / Inert atmosphere

7.1: potassium tert-butylate / toluene / 0.25 h / 25 °C / Inert atmosphere

With di-isopropyl azodicarboxylate; hydroxylamine hydrochloride; potassium tert-butylate; sodium methylate; potassium carbonate; triphenylphosphine; sodium hydroxide; silver(l) oxide; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; ethanol; ethylbenzene; water; N,N-dimethyl-formamide; toluene; 5.1: |Mitsunobu Displacement;

DOI:10.1002/anie.201304691

Reference yield:

2-(1-Hydroxy-ethylidene)-malonic acid dimethyl ester (113934-48-8) → C40H39NO9

Guidance literature:

Multi-step reaction with 8 steps

1.1: potassium carbonate / N,N-dimethyl-formamide / 17 h / 0 - 25 °C / Inert atmosphere

2.1: sodium methylate; hydroxylamine hydrochloride / methanol / 24 h / 0 - 25 °C / Inert atmosphere

3.1: silver(l) oxide / N,N-dimethyl-formamide / 18 h / 25 °C / Inert atmosphere; Darkness

4.1: sodium hydroxide / ethanol; water / 3 h / 25 °C / Inert atmosphere

5.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 3 h / Inert atmosphere; Reflux

6.1: lithium hexamethyldisilazane / tetrahydrofuran; ethylbenzene / 0.5 h / -78 °C / Inert atmosphere

6.2: 2 h / -78 °C / Inert atmosphere

7.1: potassium tert-butylate / toluene / 0.25 h / 25 °C / Inert atmosphere

8.1: ammonium fluoride; tetrabutyl ammonium fluoride / tetrahydrofuran / 0.08 h / 25 °C / Inert atmosphere; Darkness

With ammonium fluoride; di-isopropyl azodicarboxylate; hydroxylamine hydrochloride; potassium tert-butylate; tetrabutyl ammonium fluoride; sodium methylate; potassium carbonate; triphenylphosphine; sodium hydroxide; silver(l) oxide; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; ethanol; ethylbenzene; water; N,N-dimethyl-formamide; toluene; 5.1: |Mitsunobu Displacement;

DOI:10.1002/anie.201304691

upstream raw materials:

acetyl chloride

malonic acid dimethyl ester

Downstream raw materials:

methyl 3-hydroxy-5-methyl-4-isoxazolecarboxylate

3-(benzyloxy)-5-methyl-4-isoxazolecarboxylic acid

3-benzyloxy-5-methoxycarbonylmethyl-isoxazole-4-carboxylic acid methyl ester