allyl 6-methoxy-4-methyl-2-(2-phenylethynyl)-3-(1-pivaloyloxyethyl)quinoline-1(2H)-carboxylate

Base Information

Chemical Name:allyl 6-methoxy-4-methyl-2-(2-phenylethynyl)-3-(1-pivaloyloxyethyl)quinoline-1(2H)-carboxylate
CAS No.:1335060-70-2
Molecular Formula:C₃₀H₃₃NO₅
Molecular Weight:487.596
Hs Code.:

Synonyms:allyl 6-methoxy-4-methyl-2-(2-phenylethynyl)-3-(1-pivaloyloxyethyl)quinoline-1(2H)-carboxylate

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Chemical Property of allyl 6-methoxy-4-methyl-2-(2-phenylethynyl)-3-(1-pivaloyloxyethyl)quinoline-1(2H)-carboxylate

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Technology Process of allyl 6-methoxy-4-methyl-2-(2-phenylethynyl)-3-(1-pivaloyloxyethyl)quinoline-1(2H)-carboxylate

There total 10 articles about allyl 6-methoxy-4-methyl-2-(2-phenylethynyl)-3-(1-pivaloyloxyethyl)quinoline-1(2H)-carboxylate 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: 76.0%

: 1335060-65-5
1-(6-methoxy-4-methylquinolin-3-yl)ethyl pivalate

: 536-74-3
phenylacetylene

: 2937-50-0
Allyl chloroformate

: 1335060-70-2
allyl 6-methoxy-4-methyl-2-(2-phenylethynyl)-3-(1-pivaloyloxyethyl)quinoline-1(2H)-carboxylate

Guidance literature:: phenylacetylene; With isopropylmagnesium chloride; In tetrahydrofuran; at 0 - 20 ℃;

1-(6-methoxy-4-methylquinolin-3-yl)ethyl pivalate; Allyl chloroformate; In tetrahydrofuran; at -18 - 20 ℃; diastereoselective reaction;
DOI:10.1016/j.tet.2011.07.090

Reference yield:

: 1335060-55-3
1-(6-methoxy-4-methylquinolin-3-yl)ethanol

: 1335060-70-2
allyl 6-methoxy-4-methyl-2-(2-phenylethynyl)-3-(1-pivaloyloxyethyl)quinoline-1(2H)-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C

2.1: isopropylmagnesium chloride / tetrahydrofuran / 0 - 20 °C

2.2: -18 - 20 °C

With isopropylmagnesium chloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; 2.1: Reissert type reaction / 2.2: Reissert type reaction;
DOI:10.1016/j.tet.2011.07.090

Reference yield:

: 214957-88-7
2-{[(benzyloxy)carbonyl]amino}-5-hydroxybenzoic acid

: 1335060-70-2
allyl 6-methoxy-4-methyl-2-(2-phenylethynyl)-3-(1-pivaloyloxyethyl)quinoline-1(2H)-carboxylate

Guidance literature:: Multi-step reaction with 9 steps

1.1: potassium carbonate / acetone / 4 h / Reflux

2.1: n-butyllithium / tetrahydrofuran; hexane / 4 h / -78 °C

2.2: 20 °C

3.1: tetrahydrofuran / -78 - 20 °C

4.1: palladium on activated charcoal; hydrogen / ethyl acetate / 18 h / 20 °C

5.1: tetrahydrofuran / 24 h / 65 °C / Sealed tube

6.1: potassium carbonate / methanol / 22 h / 20 - 65 °C / Sealed tube

7.1: sodium tetrahydroborate / methanol / 0.25 h / 0 °C

8.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C

9.1: isopropylmagnesium chloride / tetrahydrofuran / 0 - 20 °C

9.2: -18 - 20 °C

With sodium tetrahydroborate; n-butyllithium; palladium on activated charcoal; hydrogen; isopropylmagnesium chloride; potassium carbonate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate; acetone; 9.1: Reissert type reaction / 9.2: Reissert type reaction;
DOI:10.1016/j.tet.2011.07.090