Acetonitrile, (2,3,5,6-tetrahydro-7H-indeno[5,6-b]furan-7-ylidene)- (9CI)

Base Information

• Chemical Name: Acetonitrile, (2,3,5,6-tetrahydro-7H-indeno[5,6-b]furan-7-ylidene)- (9CI)
• CAS No.: 448964-31-6
• Molecular Formula: C₁₃H₁₁NO
• Molecular Weight: 197.236
• Mol file: 448964-31-6.mol

Synonyms:Acetonitrile, (2,3,5,6-tetrahydro-7H-indeno[5,6-b]furan-7-ylidene)- (9CI);Acetonitrile, 2-(2,3,5,6-tetrahydro-7H-indeno[5,6-b]furan-7-ylidene)-

Chemical Property of Acetonitrile, (2,3,5,6-tetrahydro-7H-indeno[5,6-b]furan-7-ylidene)- (9CI)

Chemical Property:

Purity/Quality:

≥95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetonitrile, (2,3,5,6-tetrahydro-7H-indeno[5,6-b]furan-7-ylidene)- (9CI)

There total 6 articles about Acetonitrile, (2,3,5,6-tetrahydro-7H-indeno[5,6-b]furan-7-ylidene)- (9CI) 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: 66.0%

diethyl 1-cyanomethylphosphonate (2537-48-6) + 2,3,5,6-tetrahydro-7H-indeno[5,6-b]furan-7-one (448964-30-5) → 2-(2,3,5,6-tetrahydro-7H-indeno[5,6-b]furan-7-ylidene)acetonitrile (448964-31-6)

Guidance literature:

diethyl 1-cyanomethylphosphonate; With sodium hydride; In tetrahydrofuran; at 20 ℃; for 0.5h;

2,3,5,6-tetrahydro-7H-indeno[5,6-b]furan-7-one; In tetrahydrofuran; at 20 ℃; for 2h; Further stages.;

DOI:10.1021/jm0201159

Reference yield:

2.3-dihydrobenzofuran (496-16-2) → 2-(2,3,5,6-tetrahydro-7H-indeno[5,6-b]furan-7-ylidene)acetonitrile (448964-31-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 92 percent / TiCl₄ / CH₂Cl₂ / 1 h

2.1: 62 percent / pyridine; piperidine / 4 h / 100 °C

3.1: 90 percent / H₂; AcOH / 10percent Pd/C/H₂₀ / 1 h / 20 °C

4.1: SOCl₂ / 0.67 h / 75 °C

5.1: 4.09 g / AlCl₃ / 1,2-dichloro-ethane / 0.5 h / 20 °C

6.1: NaH / tetrahydrofuran / 0.5 h / 20 °C

6.2: 66 percent / tetrahydrofuran / 2 h / 20 °C

With piperidine; pyridine; aluminium trichloride; thionyl chloride; hydrogen; titanium tetrachloride; sodium hydride; acetic acid; 10percent Pd/C/H₂₀; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; 1.1: Vilsmeier-Haack reaction / 5.1: Friedel-Crafts cyclization / 6.2: Horner-Emmons reaction;

DOI:10.1021/jm0201159

Reference yield:

2,3-dihydro-benzofuran-5-carbaldehyde (55745-70-5) → 2-(2,3,5,6-tetrahydro-7H-indeno[5,6-b]furan-7-ylidene)acetonitrile (448964-31-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 62 percent / pyridine; piperidine / 4 h / 100 °C

2.1: 90 percent / H₂; AcOH / 10percent Pd/C/H₂₀ / 1 h / 20 °C

3.1: SOCl₂ / 0.67 h / 75 °C

4.1: 4.09 g / AlCl₃ / 1,2-dichloro-ethane / 0.5 h / 20 °C

5.1: NaH / tetrahydrofuran / 0.5 h / 20 °C

5.2: 66 percent / tetrahydrofuran / 2 h / 20 °C

With piperidine; pyridine; aluminium trichloride; thionyl chloride; hydrogen; sodium hydride; acetic acid; 10percent Pd/C/H₂₀; In tetrahydrofuran; 1,2-dichloro-ethane; 4.1: Friedel-Crafts cyclization / 5.2: Horner-Emmons reaction;

DOI:10.1021/jm0201159

upstream raw materials:

diethyl 1-cyanomethylphosphonate

2,3,5,6-tetrahydro-7H-indeno[5,6-b]furan-7-one

2.3-dihydrobenzofuran

2,3-dihydro-benzofuran-5-carbaldehyde

Downstream raw materials:

2-(3,5,6,7-tetrahydro-2H-indeno[5,6-b]furan-7-yl)ethylamine

Refernces