((R)-4-Benzyloxy-2-ethoxy-6-methoxy-2,3-dihydro-benzofuran-3-yl)-acetonitrile

Base Information

• Chemical Name: ((R)-4-Benzyloxy-2-ethoxy-6-methoxy-2,3-dihydro-benzofuran-3-yl)-acetonitrile
• CAS No.: 193018-51-8
• Molecular Formula: C₂₀H₂₁NO₄
• Molecular Weight: 339.391
• Mol file: 193018-51-8.mol

Synonyms:

Chemical Property of ((R)-4-Benzyloxy-2-ethoxy-6-methoxy-2,3-dihydro-benzofuran-3-yl)-acetonitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((R)-4-Benzyloxy-2-ethoxy-6-methoxy-2,3-dihydro-benzofuran-3-yl)-acetonitrile

There total 9 articles about ((R)-4-Benzyloxy-2-ethoxy-6-methoxy-2,3-dihydro-benzofuran-3-yl)-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:

2-Iodo-5-methoxy-1,3-bis-methoxymethoxy-benzene → ((R)-4-Benzyloxy-2-ethoxy-6-methoxy-2,3-dihydro-benzofuran-3-yl)-acetonitrile (193018-51-8)

Guidance literature:

Multi-step reaction with 9 steps

1: Pd(OAc)2, Ph₃P, iPr₂NEt / dimethylformamide

2: 1.) O₃; 2.) NaBH₄ / 2.) MeOH

3: diethyl ether / Ambient temperature; lipase AL originated from Achromobacter sp.

4: 89 percent / iPr₂NEt, 4-DMAP / CH₂Cl₂

5: 72 percent / 18-crown-6 / dimethylsulfoxide

6: 90 percent / LiOH / tetrahydrofuran; H₂O

7: tetra-n-propylammonium perruthenate, NMO, 4A MS / CH₂Cl₂

8: p-TsOH, HCl / ethanol

9: K₂CO₃ / dimethylformamide

With hydrogenchloride; dmap; palladium diacetate; lithium hydroxide; sodium tetrahydroborate; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 18-crown-6 ether; potassium carbonate; toluene-4-sulfonic acid; ozone; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1055/s-1997-3266

Reference yield:

2-(4-Methoxy-2,6-bis-methoxymethoxy-phenyl)-propane-1,3-diol (193018-45-0) → ((R)-4-Benzyloxy-2-ethoxy-6-methoxy-2,3-dihydro-benzofuran-3-yl)-acetonitrile (193018-51-8)

Guidance literature:

Multi-step reaction with 7 steps

1: diethyl ether / Ambient temperature; lipase AL originated from Achromobacter sp.

2: 89 percent / iPr₂NEt, 4-DMAP / CH₂Cl₂

3: 72 percent / 18-crown-6 / dimethylsulfoxide

4: 90 percent / LiOH / tetrahydrofuran; H₂O

5: tetra-n-propylammonium perruthenate, NMO, 4A MS / CH₂Cl₂

6: p-TsOH, HCl / ethanol

7: K₂CO₃ / dimethylformamide

With hydrogenchloride; dmap; lithium hydroxide; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 18-crown-6 ether; potassium carbonate; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1055/s-1997-3266

Reference yield:

(R)-4-Hydroxy-3-(4-methoxy-2,6-bis-methoxymethoxy-phenyl)-butyronitrile (193018-48-3) → ((R)-4-Benzyloxy-2-ethoxy-6-methoxy-2,3-dihydro-benzofuran-3-yl)-acetonitrile (193018-51-8)

Guidance literature:

Multi-step reaction with 3 steps

1: tetra-n-propylammonium perruthenate, NMO, 4A MS / CH₂Cl₂

2: p-TsOH, HCl / ethanol

3: K₂CO₃ / dimethylformamide

With hydrogenchloride; N-methyl-2-indolinone; tetrapropylammonium perruthennate; potassium carbonate; toluene-4-sulfonic acid; In ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1055/s-1997-3266

upstream raw materials:

benzyl chloride

((R)-2-Ethoxy-4-hydroxy-6-methoxy-2,3-dihydro-benzofuran-3-yl)-acetonitrile

2-(4-Methoxy-2,6-bis-methoxymethoxy-phenyl)-propane-1,3-diol

(R)-4-Hydroxy-3-(4-methoxy-2,6-bis-methoxymethoxy-phenyl)-butyronitrile

Downstream raw materials:

(3aR,8aS)-4-Benzyloxy-6-methoxy-2,3,3a,8a-tetrahydro-benzo[b]furo[3,2-d]furan

2-((R)-4-Benzyloxy-2-ethoxy-6-methoxy-2,3-dihydro-benzofuran-3-yl)-ethanol

Refernces