(2R-cis)-2-(2,4-difluorophenyl)-4-(5-methyl-4-oxohexyl)-2-[(1H-pyrrol-1-yl)methyl]tetrahydrofuran

Base Information

Chemical Name:(2R-cis)-2-(2,4-difluorophenyl)-4-(5-methyl-4-oxohexyl)-2-[(1H-pyrrol-1-yl)methyl]tetrahydrofuran
CAS No.:310882-16-7
Molecular Formula:C₂₂H₂₇F₂NO₂
Molecular Weight:375.459
Hs Code.:

Synonyms:(2R-cis)-2-(2,4-difluorophenyl)-4-(5-methyl-4-oxohexyl)-2-[(1H-pyrrol-1-yl)methyl]tetrahydrofuran

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Chemical Property of (2R-cis)-2-(2,4-difluorophenyl)-4-(5-methyl-4-oxohexyl)-2-[(1H-pyrrol-1-yl)methyl]tetrahydrofuran

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Technology Process of (2R-cis)-2-(2,4-difluorophenyl)-4-(5-methyl-4-oxohexyl)-2-[(1H-pyrrol-1-yl)methyl]tetrahydrofuran

There total 12 articles about (2R-cis)-2-(2,4-difluorophenyl)-4-(5-methyl-4-oxohexyl)-2-[(1H-pyrrol-1-yl)methyl]tetrahydrofuran 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:

: (E)-6-[(R)-5-(2,4-Difluoro-phenyl)-5-pyrrol-1-ylmethyl-tetrahydro-furan-3-yl]-2-methyl-hex-4-en-3-one

: 310882-16-7
(2R-cis)-2-(2,4-difluorophenyl)-4-(5-methyl-4-oxohexyl)-2-[(1H-pyrrol-1-yl)methyl]tetrahydrofuran

: 310882-34-9
6-[(3R,5R)-5-(2,4-Difluoro-phenyl)-5-pyrrol-1-ylmethyl-tetrahydro-furan-3-yl]-2-methyl-hexan-3-one

Guidance literature:: With hydrogen; palladium on activated charcoal; In ethanol; at 20 ℃;
DOI:10.1016/S0968-0896(00)00177-2

Reference yield:

: 58009-93-1
3-methyl-2-oxo-butylphosphonic acid dimethyl ester

: 310882-16-7
(2R-cis)-2-(2,4-difluorophenyl)-4-(5-methyl-4-oxohexyl)-2-[(1H-pyrrol-1-yl)methyl]tetrahydrofuran

Guidance literature:: Multi-step reaction with 2 steps

1: 1,8-diazabicyclo[5,4,0]undecen-7-ene; LiCl / acetonitrile / 3 h / 20 °C

2: 167 mg / H₂ / Pd/C / ethanol / 20 °C

With 1,8-diazabicyclo[5.4.0]-undecen-7-ene; hydrogen; lithium chloride; palladium on activated charcoal; In ethanol; acetonitrile; 1: Horner-Wadsworth-Emmons reaction / 2: Catalytic hydrogenation;
DOI:10.1016/S0968-0896(00)00177-2

Reference yield:

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

: 310882-16-7
(2R-cis)-2-(2,4-difluorophenyl)-4-(5-methyl-4-oxohexyl)-2-[(1H-pyrrol-1-yl)methyl]tetrahydrofuran

Guidance literature:: Multi-step reaction with 11 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

5.1: 88.8 percent / NaBH₄; LiCl / ethanol / 28 h / 20 °C

6.1: 4-(dimethylamino)pyridine; Et₃N / CH₂Cl₂ / 15.5 h / 20 °C

7.1: 2.34 g / NaH / toluene / 4 h / Heating

8.1: 97.2 percent / dimethylsulfoxide / 15 h / 55 °C

9.1: 68.7 percent / diisobutylaluminum hydride / toluene / -78 - 20 °C

10.1: 1,8-diazabicyclo[5,4,0]undecen-7-ene; LiCl / acetonitrile / 3 h / 20 °C

11.1: 167 mg / H₂ / Pd/C / ethanol / 20 °C

With dmap; sodium tetrahydroborate; 1,8-diazabicyclo[5.4.0]-undecen-7-ene; hydrogen; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; lithium chloride; palladium on activated charcoal; In ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; acetonitrile; 1.1: deprotonation / 1.2: Ring cleavage / 2.1: mesylation / 3.1: Cyclization / 4.1: Metallation / 4.2: Ring cleavage / 5.1: Reduction / 6.1: Tosylation / 7.1: Cyclization / 8.1: Substitution / 9.1: Reduction / 10.1: Horner-Wadsworth-Emmons reaction / 11.1: Catalytic hydrogenation;
DOI:10.1016/S0968-0896(00)00177-2