(Z)-methyl 4,4-difluoro-5-hydroxy-3-methyl-5-(4-methoxyphenyl)pent-2-enoate

Base Information

Chemical Name:(Z)-methyl 4,4-difluoro-5-hydroxy-3-methyl-5-(4-methoxyphenyl)pent-2-enoate
CAS No.:1268826-92-1
Molecular Formula:C₁₄H₁₆F₂O₄
Molecular Weight:286.275
Hs Code.:

Synonyms:(Z)-methyl 4,4-difluoro-5-hydroxy-3-methyl-5-(4-methoxyphenyl)pent-2-enoate

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Chemical Property of (Z)-methyl 4,4-difluoro-5-hydroxy-3-methyl-5-(4-methoxyphenyl)pent-2-enoate

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Technology Process of (Z)-methyl 4,4-difluoro-5-hydroxy-3-methyl-5-(4-methoxyphenyl)pent-2-enoate

There total 3 articles about (Z)-methyl 4,4-difluoro-5-hydroxy-3-methyl-5-(4-methoxyphenyl)pent-2-enoate 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: 85.0%

: 1268826-86-3
(Z)-methyl 5-(tert-butyldimethylsilyloxy)-4,4-difluoro-3-methyl-5-(4-methoxyphenyl)pent-2-enoate

: 1268826-92-1
(Z)-methyl 4,4-difluoro-5-hydroxy-3-methyl-5-(4-methoxyphenyl)pent-2-enoate

Guidance literature:: With pyridine hydrogenfluoride; In tetrahydrofuran; at 0 - 20 ℃; Inert atmosphere;
DOI:10.1021/ol103097s

Reference yield:

: 1015236-52-8
3,3-difluoro-4-hydroxy-4-(4-methoxyphenyl)butan-2-one

: 1268826-92-1
(Z)-methyl 4,4-difluoro-5-hydroxy-3-methyl-5-(4-methoxyphenyl)pent-2-enoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: 2,6-dimethylpyridine / dichloromethane / 0 - 20 °C / Inert atmosphere

2.1: 18-crown-6 ether; potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.25 h / -78 °C / Inert atmosphere

2.2: 18.5 h / -78 - -40 °C / Inert atmosphere

3.1: pyridine hydrogenfluoride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

With 2,6-dimethylpyridine; 18-crown-6 ether; potassium hexamethylsilazane; pyridine hydrogenfluoride; In tetrahydrofuran; dichloromethane; toluene; 2.1: Still-Gennari olefination / 2.2: Still-Gennari olefination;
DOI:10.1021/ol103097s

Reference yield:

: 1268826-76-1
4-(tert-butyldimethylsilyloxy)-3,3-difluoro-4-(4-methoxyphenyl)butan-2-one

: 1268826-92-1
(Z)-methyl 4,4-difluoro-5-hydroxy-3-methyl-5-(4-methoxyphenyl)pent-2-enoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: 18-crown-6 ether; potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.25 h / -78 °C / Inert atmosphere

1.2: 18.5 h / -78 - -40 °C / Inert atmosphere

2.1: pyridine hydrogenfluoride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

With 18-crown-6 ether; potassium hexamethylsilazane; pyridine hydrogenfluoride; In tetrahydrofuran; toluene; 1.1: Still-Gennari olefination / 1.2: Still-Gennari olefination;
DOI:10.1021/ol103097s