E-3-(5-benzylidene-2-oxo-5,6-dihydro-2H-pyran-3-yl)propionic acid methyl ester

Base Information

Chemical Name:E-3-(5-benzylidene-2-oxo-5,6-dihydro-2H-pyran-3-yl)propionic acid methyl ester
CAS No.:518358-05-9
Molecular Formula:C₁₆H₁₆O₄
Molecular Weight:272.301
Hs Code.:

Synonyms:E-3-(5-benzylidene-2-oxo-5,6-dihydro-2H-pyran-3-yl)propionic acid methyl ester

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Chemical Property of E-3-(5-benzylidene-2-oxo-5,6-dihydro-2H-pyran-3-yl)propionic acid methyl ester

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Technology Process of E-3-(5-benzylidene-2-oxo-5,6-dihydro-2H-pyran-3-yl)propionic acid methyl ester

There total 8 articles about E-3-(5-benzylidene-2-oxo-5,6-dihydro-2H-pyran-3-yl)propionic acid methyl ester 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: 31.0%

: 1445-45-0
Trimethyl orthoacetate

: 518358-01-5
methyl (Z)-4-{[(tert-butyl)dimethylsilyloxy]methyl}-3-hydroxy-2-methylene-5-phenylpent-4-enoate

: 518358-05-9
E-3-(5-benzylidene-2-oxo-5,6-dihydro-2H-pyran-3-yl)propionic acid methyl ester

Guidance literature:: With propionic acid; for 15h; Heating;
DOI:10.1002/1522-2675(200211)85:11<3994::AID-HLCA3994>3.0.CO;2-2

Reference yield:

: 859427-83-1
4-hydroxy-5-hydroxymethyl-3-methylenetetrahydropyran-2-one

: 518358-05-9
E-3-(5-benzylidene-2-oxo-5,6-dihydro-2H-pyran-3-yl)propionic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 65 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 96 h / 20 °C

2: 76 percent / propionic acid / 48 h / Heating

3: 34 percent / Bu₄NF / tetrahydrofuran / 2 h

4: PPh₃; AgOAc; Pd(OAc)2 / acetonitrile / 24 h / Heating

With dmap; palladium diacetate; tetrabutyl ammonium fluoride; silver(I) acetate; propionic acid; triphenylphosphine; In tetrahydrofuran; dichloromethane; acetonitrile; 2: Claisen rearrangement / 4: Heck reaction;
DOI:10.1016/j.bmc.2005.03.037

Reference yield:

: 859427-79-5
2-{hydroxy-[2-(4-methoxyphenyl)-[1,3]dioxan-5-yl]methyl}acrylic acid methyl ester

: 518358-05-9
E-3-(5-benzylidene-2-oxo-5,6-dihydro-2H-pyran-3-yl)propionic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: H₂SO₄ / 20 °C

1.2: 72 percent / Bu₄NF / tetrahydrofuran / 2 h / 20 °C

2.1: 65 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 96 h / 20 °C

3.1: 76 percent / propionic acid / 48 h / Heating

4.1: 34 percent / Bu₄NF / tetrahydrofuran / 2 h

5.1: PPh₃; AgOAc; Pd(OAc)2 / acetonitrile / 24 h / Heating

With dmap; palladium diacetate; sulfuric acid; tetrabutyl ammonium fluoride; silver(I) acetate; propionic acid; triphenylphosphine; In tetrahydrofuran; dichloromethane; acetonitrile; 3.1: Claisen rearrangement / 5.1: Heck reaction;
DOI:10.1016/j.bmc.2005.03.037