(5-benzyloxy-7-methoxy-6-methylisoquinol-1-yl)methyl angelate

Base Information

Chemical Name:(5-benzyloxy-7-methoxy-6-methylisoquinol-1-yl)methyl angelate
CAS No.:690254-83-2
Molecular Formula:C₂₄H₂₅NO₄
Molecular Weight:391.467
Hs Code.:

Synonyms:(5-benzyloxy-7-methoxy-6-methylisoquinol-1-yl)methyl angelate

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Chemical Property of (5-benzyloxy-7-methoxy-6-methylisoquinol-1-yl)methyl angelate

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Technology Process of (5-benzyloxy-7-methoxy-6-methylisoquinol-1-yl)methyl angelate

There total 7 articles about (5-benzyloxy-7-methoxy-6-methylisoquinol-1-yl)methyl angelate 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: 78.0%

: 137601-32-2
(2Z)-2-methyl-2-butenoic 2,4,6-trichlorobenzoic anhydride

: 258289-47-3
5-benzyloxy-1-hydroxymethyl-7-methoxy-6-methylisoquinoline

: 690254-83-2
(5-benzyloxy-7-methoxy-6-methylisoquinol-1-yl)methyl angelate

Guidance literature:: 5-benzyloxy-1-hydroxymethyl-7-methoxy-6-methylisoquinoline; With phenyllithium; In 1,4-dioxane; diethyl ether; cyclohexane; for 0.166667h; cooling;

(2Z)-2-methyl-2-butenoic 2,4,6-trichlorobenzoic anhydride; In 1,4-dioxane; diethyl ether; cyclohexane; at 20 ℃; for 12h; Further stages.;
DOI:10.1016/j.tet.2004.02.010

Reference yield:

: 54700-36-6
2-hydroxy-4-methoxy-3-methylbenzaldehyde

: 690254-83-2
(5-benzyloxy-7-methoxy-6-methylisoquinol-1-yl)methyl angelate

Guidance literature:: Multi-step reaction with 12 steps

1.1: 99 percent / K₂CO₃ / dimethylformamide / 4 h / 60 °C

2.1: 88 percent / mCPBA / CH₂Cl₂ / 1 h / 60 °C

3.1: 53 percent / AcOH / 3 h / 110 °C

4.1: 81 percent / pyridine / CH₂Cl₂ / 1 h / cooling

5.1: 90 percent / Et₄NCl; PdCl₂(PPh₃)2 / dimethylformamide / 1.5 h / 110 °C

6.1: Mg; 1,2-dibromoethane / tetrahydrofuran

6.2: tetrahydrofuran / 2 h / 20 °C

6.3: 87 percent / H₂O₂; KHCO₃; KF / tetrahydrofuran; methanol / 3 h / 20 °C

7.1: 92 percent / imidazole / dimethylformamide / 1 h / 20 °C

8.1: 85 percent / pyridinium chlorochromate; celite / CH₂Cl₂ / 10 h / 20 °C

9.1: 57 percent / NH₂OH*HCl; AcONa / ethanol / 1 h / 85 °C

10.1: 49 percent / various solvent(s) / 1 h / 180 °C

11.1: 89 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C

12.1: PhLi / cyclohexane; diethyl ether; dioxane / 0.17 h / cooling

12.2: 78 percent / cyclohexane; diethyl ether; dioxane / 12 h / 20 °C

With pyridine; 1H-imidazole; bis-triphenylphosphine-palladium(II) chloride; Celite; hydroxylamine hydrochloride; tetraethylammonium chloride; tetrabutyl ammonium fluoride; sodium acetate; potassium carbonate; magnesium; acetic acid; phenyllithium; ethylene dibromide; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; In tetrahydrofuran; 1,4-dioxane; diethyl ether; ethanol; dichloromethane; cyclohexane; N,N-dimethyl-formamide; 2.1: Baeyer-Villiger reaction / 3.1: Duff reaction / 6.2: Grignard reaction;
DOI:10.1016/j.tet.2004.02.010

Reference yield:

: 105103-95-5
2-(benzyloxy)-4-methoxy-3-methylphenol

: 690254-83-2
(5-benzyloxy-7-methoxy-6-methylisoquinol-1-yl)methyl angelate

Guidance literature:: Multi-step reaction with 10 steps

1.1: 53 percent / AcOH / 3 h / 110 °C

2.1: 81 percent / pyridine / CH₂Cl₂ / 1 h / cooling

3.1: 90 percent / Et₄NCl; PdCl₂(PPh₃)2 / dimethylformamide / 1.5 h / 110 °C

4.1: Mg; 1,2-dibromoethane / tetrahydrofuran

4.2: tetrahydrofuran / 2 h / 20 °C

4.3: 87 percent / H₂O₂; KHCO₃; KF / tetrahydrofuran; methanol / 3 h / 20 °C

5.1: 92 percent / imidazole / dimethylformamide / 1 h / 20 °C

6.1: 85 percent / pyridinium chlorochromate; celite / CH₂Cl₂ / 10 h / 20 °C

7.1: 57 percent / NH₂OH*HCl; AcONa / ethanol / 1 h / 85 °C

8.1: 49 percent / various solvent(s) / 1 h / 180 °C

9.1: 89 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C

10.1: PhLi / cyclohexane; diethyl ether; dioxane / 0.17 h / cooling

10.2: 78 percent / cyclohexane; diethyl ether; dioxane / 12 h / 20 °C

With pyridine; 1H-imidazole; bis-triphenylphosphine-palladium(II) chloride; Celite; hydroxylamine hydrochloride; tetraethylammonium chloride; tetrabutyl ammonium fluoride; sodium acetate; magnesium; acetic acid; phenyllithium; ethylene dibromide; pyridinium chlorochromate; In tetrahydrofuran; 1,4-dioxane; diethyl ether; ethanol; dichloromethane; cyclohexane; N,N-dimethyl-formamide; 1.1: Duff reaction / 4.2: Grignard reaction;
DOI:10.1016/j.tet.2004.02.010