p-Toluenesulfonic acid → HCID 59226560, compound

HRID 879158Notes

Reaction equation

HRID 879158 reaction equation
[CH3:1][CH:2]1[CH2:7][CH:6](O)[CH:5]=[C:4]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2[N+:15]([O-:17])=[O:16])[CH2:3]1.CC1C=CC(S(O)(=O)=O)=CC=1.CCOC(C)=O>O1CCOCC1>[CH3:1][CH:2]1[CH2:3][C:4]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2[N+:15]([O-:17])=[O:16])=[CH:5][CH:6]=[CH:7]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 8857Ethyl AcetateHCID 671307105-Methyl-3-(3-nitropyridin-4-yl)cyclohex-2-enol

Product 1

HCID 59226560HCID 59226560, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of (+/−)-5-methyl-3-(3-nitropyridin-4-yl)cyclohex-2-enol (1.0 equiv.) in dioxane (0.1 M) was added p-TSA (1.0 equiv.), and the reaction was stirred at 100° C. for 3 h. The solution was cooled to room temperature, then passed through a pad of neutral alumina eluting with EtOAc to yield (+/−)-4-(5-methylcyclohexa-1,3-dienyl)-3-nitropyridine as a yellow oil in 68% yield. LC/MS=217.1 (M+H), LC=3.908 min.

Workup

  1. temperatureThe solution was cooled to room temperature

Sources & evidence

ORD record
ord-9b21d16dc2b84aa1a4bb9825017a46d3
Source dataset
uspto-grants-2015_03
Patent number
US08987457B2

Reaction notes

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