4-Carbomethoxytetrahydro-3-thiophenone, Tech.

Base Information

• Chemical Name: 4-Carbomethoxytetrahydro-3-thiophenone, Tech.
• CAS No.: 22097-90-1
• Molecular Formula: C₆H₈O₃S
• Molecular Weight: 160.194
• Mol file: 22097-90-1.mol

Synonyms:

Chemical Property of 4-Carbomethoxytetrahydro-3-thiophenone, Tech.

Chemical Property:

• Vapor Pressure: 0.0243mmHg at 25°C
• Boiling Point: 248.4°Cat760mmHg
• Flash Point: 116.7°C
• Density: 1.309g/cm³

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4-Carbomethoxytetrahydro-3-thiophenone, Tech.

There total 1 articles about 4-Carbomethoxytetrahydro-3-thiophenone, Tech. 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: 35.0%

Methyl thioglycolate (2365-48-2) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → 2,5-dihydro-4-hydroxy-3-thiophenecarboxylic acid methyl ester (22097-90-1)

Guidance literature:

With sodium hydride; In 1,2-dimethoxyethane; at 0 ℃; for 5h; Inert atmosphere;

DOI:10.1021/jacs.0c12194

Reference yield:

2,5-dihydro-4-hydroxy-3-thiophenecarboxylic acid methyl ester (22097-90-1) → C13H14OS

Guidance literature:

Multi-step reaction with 8 steps

1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 0 - 23 °C / Inert atmosphere

2.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium hydroxide / toluene; water / 1 h / 110 °C

3.1: isopropylmagnesium chloride / tetrahydrofuran / 3 h / -18 °C / Inert atmosphere

4.1: tetrahydrofuran / 2 h / -78 - 23 °C

5.1: dichloromethane / 1 h / 23 °C / Inert atmosphere

6.1: triethylamine / dichloromethane / 3 h / 23 °C / Inert atmosphere

7.1: N-chloro-succinimide / dichloromethane-d2 / 0.17 h / 0 °C

7.2: 3 h / 0 °C

8.1: lithium triethylborohydride / tetrahydrofuran / 1 h / -78 - 23 °C

With N-chloro-succinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; isopropylmagnesium chloride; lithium triethylborohydride; triethylamine; N-ethyl-N,N-diisopropylamine; potassium hydroxide; In tetrahydrofuran; dichloromethane; dichloromethane-d2; water; toluene;

DOI:10.1021/jacs.0c12194

Reference yield:

2,5-dihydro-4-hydroxy-3-thiophenecarboxylic acid methyl ester (22097-90-1) → C14H17NO2S

Guidance literature:

Multi-step reaction with 10 steps

1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 0 - 23 °C / Inert atmosphere

2.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium hydroxide / toluene; water / 1 h / 110 °C

3.1: isopropylmagnesium chloride / tetrahydrofuran / 3 h / -18 °C / Inert atmosphere

4.1: tetrahydrofuran / 2 h / -78 - 23 °C

5.1: dichloromethane / 1 h / 23 °C / Inert atmosphere

6.1: triethylamine / dichloromethane / 3 h / 23 °C / Inert atmosphere

7.1: water; N-chloro-succinimide / 20 h / 23 °C

8.1: oxalyl dichloride / dichloromethane / 0.5 h / 0 - 23 °C

9.1: dilithium tetrachlorocuprate / tetrahydrofuran / 23 °C / Inert atmosphere

9.2: 0.5 h / 0 °C

10.1: [bis(acetoxy)iodo]benzene; ammonium carbamate / methanol / 3 h / 0 °C

With N-chloro-succinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; oxalyl dichloride; dilithium tetrachlorocuprate; [bis(acetoxy)iodo]benzene; water; isopropylmagnesium chloride; ammonium carbamate; triethylamine; N-ethyl-N,N-diisopropylamine; potassium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water; toluene;

DOI:10.1021/jacs.0c12194

upstream raw materials:

Methyl thioglycolate

acrylic acid methyl ester