4-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl)(hydroxy)methyl]-N,N-diethylbenzamide

Base Information

Chemical Name:4-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl)(hydroxy)methyl]-N,N-diethylbenzamide
CAS No.:308110-32-9
Molecular Formula:C₂₂H₂₇NO₃
Molecular Weight:353.461
Hs Code.:

Synonyms:4-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl)(hydroxy)methyl]-N,N-diethylbenzamide

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Chemical Property of 4-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl)(hydroxy)methyl]-N,N-diethylbenzamide

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Technology Process of 4-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl)(hydroxy)methyl]-N,N-diethylbenzamide

There total 5 articles about 4-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl)(hydroxy)methyl]-N,N-diethylbenzamide 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: 67.0%

: 77350-52-8
N,N-diethyl-4-iodobenzamide

: 38002-88-9
2,3-dihydro-2,2-dimethylbenzofuran-7-carboxaldehyde

: 308110-32-9
4-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl)(hydroxy)methyl]-N,N-diethylbenzamide

Guidance literature:: N,N-diethyl-4-iodobenzamide; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

2,3-dihydro-2,2-dimethylbenzofuran-7-carboxaldehyde; In tetrahydrofuran; hexane; for 1h; Further stages.;
DOI:10.1021/jm000228x

Reference yield:

: 1563-38-8
2,3-dihydro-2,2-dimethylbenzofuran-7-ol

: 308110-32-9
4-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl)(hydroxy)methyl]-N,N-diethylbenzamide

Guidance literature:: Multi-step reaction with 5 steps

1.1: pyridine / CH₂Cl₂ / 1 h / 25 °C

2.1: Et₃N; Pd(OAc)2; bis-diphenylphosphinoferrocene / methanol; dimethylsulfoxide / 16 h / 70 °C

3.1: DIBAl / toluene / 0.5 h / -78 °C

4.1: pyridinium dichromate / CH₂Cl₂ / 40 °C

5.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

5.2: 67 percent / tetrahydrofuran; hexane / 1 h

With pyridine; 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; dipyridinium dichromate; n-butyllithium; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; dimethyl sulfoxide; toluene; 1.1: triflation / 2.1: carbomethoxylation / 3.1: Reduction / 4.1: Oxidation / 5.1: Metallation / 5.2: Addition;
DOI:10.1021/jm000228x

Reference yield:

: 99517-60-9
methyl 2,2-dimethyl-2,3-dihydro-1-benzofuran-7-carboxylate

: 308110-32-9
4-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl)(hydroxy)methyl]-N,N-diethylbenzamide

Guidance literature:: Multi-step reaction with 3 steps

1.1: DIBAl / toluene / 0.5 h / -78 °C

2.1: pyridinium dichromate / CH₂Cl₂ / 40 °C

3.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

3.2: 67 percent / tetrahydrofuran; hexane / 1 h

With dipyridinium dichromate; n-butyllithium; diisobutylaluminium hydride; In tetrahydrofuran; hexane; dichloromethane; toluene; 1.1: Reduction / 2.1: Oxidation / 3.1: Metallation / 3.2: Addition;
DOI:10.1021/jm000228x