ethyl (5R-cis)- and (5R-trans)-5-(2,4-difluorophenyl)-2-oxo-5-[(1H-pyrrol-1-yl)methyl]-3-tetrahydrofurancarboxylate

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Chemical Name:ethyl (5R-cis)- and (5R-trans)-5-(2,4-difluorophenyl)-2-oxo-5-[(1H-pyrrol-1-yl)methyl]-3-tetrahydrofurancarboxylate
CAS No.:310882-03-2
Molecular Formula:C₁₈H₁₇F₂NO₄
Molecular Weight:349.334
Hs Code.:

Synonyms:ethyl (5R-cis)- and (5R-trans)-5-(2,4-difluorophenyl)-2-oxo-5-[(1H-pyrrol-1-yl)methyl]-3-tetrahydrofurancarboxylate

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Chemical Property of ethyl (5R-cis)- and (5R-trans)-5-(2,4-difluorophenyl)-2-oxo-5-[(1H-pyrrol-1-yl)methyl]-3-tetrahydrofurancarboxylate

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Technology Process of ethyl (5R-cis)- and (5R-trans)-5-(2,4-difluorophenyl)-2-oxo-5-[(1H-pyrrol-1-yl)methyl]-3-tetrahydrofurancarboxylate

There total 4 articles about ethyl (5R-cis)- and (5R-trans)-5-(2,4-difluorophenyl)-2-oxo-5-[(1H-pyrrol-1-yl)methyl]-3-tetrahydrofurancarboxylate 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: 70.2%

: 105-53-3
diethyl malonate

: (2R)-2-(2,4-difluorophenyl)-2-[(1H-pyrrol-1-yl)methyl]oxirane

: 310882-03-2
ethyl (5R-cis)- and (5R-trans)-5-(2,4-difluorophenyl)-2-oxo-5-[(1H-pyrrol-1-yl)methyl]-3-tetrahydrofurancarboxylate

Guidance literature:: diethyl malonate; With sodium hydride; dimethyl sulfoxide; at 20 ℃; for 1h;

(2R)-2-(2,4-difluorophenyl)-2-[(1H-pyrrol-1-yl)methyl]oxirane; In dimethyl sulfoxide; at 75 - 80 ℃; for 30h;
DOI:10.1016/S0968-0896(00)00177-2

Reference yield:

: 141113-37-3
(S)-(2-(2,4-difluorophenyl)oxiran-2-yl)methanol

: 310882-03-2
ethyl (5R-cis)- and (5R-trans)-5-(2,4-difluorophenyl)-2-oxo-5-[(1H-pyrrol-1-yl)methyl]-3-tetrahydrofurancarboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: NaH / dimethylformamide / 0 - 20 °C

1.2: 46.2 percent / dimethylformamide / 2.5 h / 50 - 60 °C

2.1: Et₃N / CH₂Cl₂ / 2 h / 20 °C

3.1: 2.61 g / NaH / dimethylformamide / 4 h / 20 °C

4.1: NaH; DMSO / 1 h / 20 °C

4.2: 70.2 percent / dimethylsulfoxide / 30 h / 75 - 80 °C

With sodium hydride; dimethyl sulfoxide; triethylamine; In dichloromethane; N,N-dimethyl-formamide; 1.1: deprotonation / 1.2: Ring cleavage / 2.1: mesylation / 3.1: Cyclization / 4.1: Metallation / 4.2: Ring cleavage;
DOI:10.1016/S0968-0896(00)00177-2

Reference yield:

: 310881-99-3
(2R)-2-(2,4-difluorophenyl)-3-(1H-pyrrol-1-yl)-1,2-propanediol

: 310882-03-2
ethyl (5R-cis)- and (5R-trans)-5-(2,4-difluorophenyl)-2-oxo-5-[(1H-pyrrol-1-yl)methyl]-3-tetrahydrofurancarboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: Et₃N / CH₂Cl₂ / 2 h / 20 °C

2.1: 2.61 g / NaH / dimethylformamide / 4 h / 20 °C

3.1: NaH; DMSO / 1 h / 20 °C

3.2: 70.2 percent / dimethylsulfoxide / 30 h / 75 - 80 °C

With sodium hydride; dimethyl sulfoxide; triethylamine; In dichloromethane; N,N-dimethyl-formamide; 1.1: mesylation / 2.1: Cyclization / 3.1: Metallation / 3.2: Ring cleavage;
DOI:10.1016/S0968-0896(00)00177-2