p-Toluenesulfonic acid → Ethyl 6-oxo-2-(pentafluoroethyl)-1,4,5,6-tetrahydropyridine-3-carboxylate

HRID 2421029

Reaction equation

HRID 2421029 reaction equation
[C:1]([NH2:5])(=[O:4])[CH:2]=[CH2:3].[F:6][C:7]([F:20])([C:16]([F:19])([F:18])[F:17])[C:8](=O)[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11].C1(C)C=CC(S(O)(=O)=O)=CC=1>ClC1C=CC=CC=1>[O:4]=[C:1]1[NH:5][C:8]([C:7]([F:6])([F:20])[C:16]([F:18])([F:17])[F:19])=[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 6579AcrylamideHCID 522203Ethyl 4,4,5,5,5-Pentafluoro-3-oxovalerate

Product 1

HCID 86611248Ethyl 6-oxo-2-(pentafluoroethyl)-1,4,5,6-tetrahydropyridine-3-carboxylateYield 4.2%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
120 °C

Procedure

A suspension of acrylamide (4.11 g), ethyl 4,4,5,5,5-pentafluoro-3-oxopentanoate (16.5 g) and p-toluenesulphonic acid (0.120 g) in chlorobenzene (40 mL) was sonicated for 30 minutes then heated by microwave irradiation (150 W, 120° C.) for 3 h. The reaction mixture was concentrated in vacuo and subjected to flash column chromatography (eluent 1:3 ethyl acetate/isohexane) to yield a colourless solid (0.697 g).

Workup

  1. customwas sonicated for 30 minutes
  2. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-66b8a55bacc44fc0b2643845168c18ad
Source dataset
uspto-grants-2011_06
Patent number
US07956070B2

Linked notes

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