methyl 1-(3,4-dihydro-2H-pyran-6-carbonyl)-2-(4-methoxyphenyl)cyclopropanecarboxylate

Base Information

• Chemical Name: methyl 1-(3,4-dihydro-2H-pyran-6-carbonyl)-2-(4-methoxyphenyl)cyclopropanecarboxylate
• CAS No.: 1258518-01-2
• Molecular Formula: C₁₈H₂₀O₅
• Molecular Weight: 316.354
• Mol file: 1258518-01-2.mol

Synonyms:methyl 1-(3,4-dihydro-2H-pyran-6-carbonyl)-2-(4-methoxyphenyl)cyclopropanecarboxylate

Chemical Property of methyl 1-(3,4-dihydro-2H-pyran-6-carbonyl)-2-(4-methoxyphenyl)cyclopropanecarboxylate

Chemical Property:

Purity/Quality:

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Technology Process of methyl 1-(3,4-dihydro-2H-pyran-6-carbonyl)-2-(4-methoxyphenyl)cyclopropanecarboxylate

There total 1 articles about methyl 1-(3,4-dihydro-2H-pyran-6-carbonyl)-2-(4-methoxyphenyl)cyclopropanecarboxylate 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: 55.0%

3,4-dihydro-2H-pyran (110-87-2) + methyl 1-(methoxy(methyl)carbamoyl)-2-(4-methoxyphenyl)cyclopropane-1-carboxylate (1258518-10-3) → methyl 1-(3,4-dihydro-2H-pyran-6-carbonyl)-2-(4-methoxyphenyl)cyclopropanecarboxylate (1258518-01-2)

Guidance literature:

3,4-dihydro-2H-pyran; With tert.-butyl lithium; In tetrahydrofuran; pentane; at -78 ℃; Inert atmosphere; Cooling with ice;

methyl 1-(methoxy(methyl)carbamoyl)-2-(4-methoxyphenyl)cyclopropane-1-carboxylate; In tetrahydrofuran; pentane; at -78 - 20 ℃; Inert atmosphere;

DOI:10.1021/ol102497w

Reference yield: 92.6%

methyl 1-(3,4-dihydro-2H-pyran-6-carbonyl)-2-(4-methoxyphenyl)cyclopropanecarboxylate (1258518-01-2) → methyl 5-(4-methoxyphenyl)-8-oxo-3,4,5,6,7,8-hexahydro-2H-chromene-7-carboxylate (1258518-27-2)

Guidance literature:

With indium(III) triflate; In dichloromethane; at 0 ℃; for 0.5h; Inert atmosphere;

DOI:10.1021/ol102497w

Reference yield:

methyl 1-(3,4-dihydro-2H-pyran-6-carbonyl)-2-(4-methoxyphenyl)cyclopropanecarboxylate (1258518-01-2) → 5-(4-methoxyphenyl)-3,4,6,7-tetrahydro-2H-chromen-8(5H)-one + 5-(4-methoxyphenyl)-3,4,6,7-tetrahydro-2H-chromen-8(5H)-one

Guidance literature:

Multi-step reaction with 2 steps

1: toluene-4-sulfonic acid / acetonitrile / 0.25 h / 20 °C / Inert atmosphere

2: sodium chloride / water; dimethyl sulfoxide / 0.5 h / 150 °C / Inert atmosphere; Microwave irradiation

With toluene-4-sulfonic acid; sodium chloride; In water; dimethyl sulfoxide; acetonitrile; 1: Nazarov cyclization;

DOI:10.1002/chem.201102583

upstream raw materials:

3,4-dihydro-2H-pyran

methyl 1-(methoxy(methyl)carbamoyl)-2-(4-methoxyphenyl)cyclopropane-1-carboxylate

Downstream raw materials:

methyl 5-(4-methoxyphenyl)-8-oxo-3,4,5,6,7,8-hexahydro-2H-chromene-7-carboxylate