Phenyl(tetrahydro-2H-pyran-2-yloxy)acetonitrile

Base Information

• Chemical Name: Phenyl(tetrahydro-2H-pyran-2-yloxy)acetonitrile
• CAS No.: 41865-47-8
• Molecular Formula: C13H15NO2
• Molecular Weight: 217.268
• DSSTox Substance ID: DTXSID501221012
• Nikkaji Number: J2.327.833B
• Mol file: 41865-47-8.mol

Synonyms:Phenyl(tetrahydro-2H-pyran-2-yloxy)acetonitrile;SCHEMBL4052862;MVSFLKZTEIXNEN-UHFFFAOYSA-N;DTXSID501221012;41865-47-8;alpha-[(Tetrahydro-2H-pyran-2-yl)oxy]benzeneacetonitrile

Chemical Property of Phenyl(tetrahydro-2H-pyran-2-yloxy)acetonitrile

Chemical Property:

• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 217.110278721
• Heavy Atom Count: 16
• Complexity: 252

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCOC(C1)OC(C#N)C2=CC=CC=C2

Technology Process of Phenyl(tetrahydro-2H-pyran-2-yloxy)acetonitrile

There total 2 articles about Phenyl(tetrahydro-2H-pyran-2-yloxy)acetonitrile 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: 95.0%

2-acetoxytetrahydropyran (2761-33-3) + trimethylsilyl cyanide (7677-24-9) + benzaldehyde (100-52-7) → 2-<(2-tetrahydropyranyl)oxy>-2-phenylacetonitrile (41865-47-8)

Guidance literature:

trimethylsilyl cyanide; benzaldehyde; iron(III) trifluoromethanesulfonate; In various solvent(s); at 0 ℃; for 0.5h;

2-acetoxytetrahydropyran; In various solvent(s); at -78 ℃; for 1h;

DOI:10.1016/j.tetlet.2006.04.106

Reference yield:

sodium hydroxy(phenyl)methanesulfonate (4657-12-9) → 2-<(2-tetrahydropyranyl)oxy>-2-phenylacetonitrile (41865-47-8)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂O

2: 36percent HCl / Ambient temperature

With hydrogenchloride; In water;

Reference yield: 88.0%

diallylcarbonate (15022-08-9) + 2-<(2-tetrahydropyranyl)oxy>-2-phenylacetonitrile (41865-47-8) → 2-Phenyl-2-(tetrahydro-pyran-2-yloxy)-pent-4-enenitrile (95514-58-2)

Guidance literature:

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; 1,2-bis-(diphenylphosphino)ethane; In tetrahydrofuran; at 65 ℃; for 1h;

DOI:10.1021/jo00209a032

upstream raw materials:

2-acetoxytetrahydropyran

trimethylsilyl cyanide

benzaldehyde

sodium hydroxy(phenyl)methanesulfonate

Downstream raw materials:

2-Phenyl-2-(tetrahydro-pyran-2-yloxy)-pent-4-enenitrile

γ-fluorobutyrophenone

α-(tetrahydropyranyloxy)phenylacetamidine hydrochloride

4-hydroxy-3-methyl-5-phenylfuran-2(5H)-one