(E)-6-benzylidene-4-ethyl-3,10-dioxo-3,4,6,7,8,10-hexahydro-1H-pyrano[3,4-f]indolizine-5-carboxylic acid

Base Information

Chemical Name:(E)-6-benzylidene-4-ethyl-3,10-dioxo-3,4,6,7,8,10-hexahydro-1H-pyrano[3,4-f]indolizine-5-carboxylic acid
CAS No.:145474-13-1
Molecular Formula:C₂₁H₁₉NO₅
Molecular Weight:365.386
Hs Code.:

Synonyms:(E)-6-benzylidene-4-ethyl-3,10-dioxo-3,4,6,7,8,10-hexahydro-1H-pyrano[3,4-f]indolizine-5-carboxylic acid

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Chemical Property of (E)-6-benzylidene-4-ethyl-3,10-dioxo-3,4,6,7,8,10-hexahydro-1H-pyrano[3,4-f]indolizine-5-carboxylic acid

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Technology Process of (E)-6-benzylidene-4-ethyl-3,10-dioxo-3,4,6,7,8,10-hexahydro-1H-pyrano[3,4-f]indolizine-5-carboxylic acid

There total 5 articles about (E)-6-benzylidene-4-ethyl-3,10-dioxo-3,4,6,7,8,10-hexahydro-1H-pyrano[3,4-f]indolizine-5-carboxylic acid 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: 90.0%

: 100-52-7
benzaldehyde

: 145474-08-4
4-ethyl-3,10-dioxo-1H,3H,4H,6H,7H,8H,10H-pyrano[3,4-f]indolizine-5-carboxylic acid methyl ester

: 145474-13-1
(E)-6-benzylidene-4-ethyl-3,10-dioxo-3,4,6,7,8,10-hexahydro-1H-pyrano[3,4-f]indolizine-5-carboxylic acid

Guidance literature:: With sodium hexamethyldisilazane; In tetrahydrofuran; for 16h; -70 deg C to room temperature;
DOI:10.1021/jo00055a012

Reference yield:

: 145474-07-3
methyl 7-[1-(methoxycarbonyl)propyl]-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxylate

: 145474-13-1
(E)-6-benzylidene-4-ethyl-3,10-dioxo-3,4,6,7,8,10-hexahydro-1H-pyrano[3,4-f]indolizine-5-carboxylic acid

Guidance literature:: Multi-step reaction with 2 steps

1: 95 percent / aq. H₂SO₄ / dioxane / 24 h / 107 °C

2: 90 percent / sodium hexamethyldisilazide / tetrahydrofuran / 16 h / -70 deg C to room temperature

With sulfuric acid; sodium hexamethyldisilazane; In tetrahydrofuran; 1,4-dioxane;
DOI:10.1021/jo00055a012

Reference yield:

: 120461-65-6
dimethyl 3-chloro-2-pentenedioate

: 145474-13-1
(E)-6-benzylidene-4-ethyl-3,10-dioxo-3,4,6,7,8,10-hexahydro-1H-pyrano[3,4-f]indolizine-5-carboxylic acid

Guidance literature:: Multi-step reaction with 4 steps

1: 92 percent / Et₃N / ethanol / 65 h / Ambient temperature

2: 1) tBuOK / 1) DME, -70 deg C, 20 min, 2a) -70 deg C to room temperature, b) room temperature, 30 h

3: 95 percent / aq. H₂SO₄ / dioxane / 24 h / 107 °C

4: 90 percent / sodium hexamethyldisilazide / tetrahydrofuran / 16 h / -70 deg C to room temperature

With sulfuric acid; potassium tert-butylate; sodium hexamethyldisilazane; triethylamine; In tetrahydrofuran; 1,4-dioxane; ethanol;
DOI:10.1021/jo00055a012