Ethanol → Methyl 3-(2,5-dimethyl-1H-pyrrol-1-yl)-6-ethoxy-5-(trifluoromethyl)picolinate

HRID 2202518Notes

Reaction equation

HRID 2202518 reaction equation
[CH3:1][C:2]1[N:3]([C:8]2[C:9]([C:19]([O:21][CH3:22])=[O:20])=[N:10][C:11]([OH:18])=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:13]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1.[CH3:23][CH2:24]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCOCC1>[CH3:7][C:4]1[N:3]([C:8]2[C:9]([C:19]([O:21][CH3:22])=[O:20])=[N:10][C:11]([O:18][CH2:23][CH3:24])=[C:12]([C:14]([F:15])([F:16])[F:17])[CH:13]=2)[C:2]([CH3:1])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 178499131Methyl 3-(2,5-dimethyl-1H-pyrrol-1-yl)-6-hydroxy-5-(trifluoromethyl)picolinate

Product 1

HCID 67383877Methyl 3-(2,5-dimethyl-1H-pyrrol-1-yl)-6-ethoxy-5-(trifluoromethyl)picolinate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Methyl 3-(2,5-dimethyl-1H-pyrrol-1-yl)-6-hydroxy-5-(trifluoromethyl)picolinate (62 mg, 0.168 mmol) in 1,4-dioxane (1.5 ml) (dry) was treated with EtOH (0.020 ml, 0.335 mmol) and triphenylphosphine (88 mg, 0.335 mmol) and the solution stirred. DEAD (0.053 ml, 0.335 mmol) was added dropwise and the reaction mixture stirred at room temperature for 2 hours. The solvent was removed in vacuo and purification of the crude product by chromatography on silica eluting with iso-hexane: EtOAc (gradient of 0 to 10% EtOAc) afforded the title compound;

Workup

  1. stirringthe reaction mixture stirred at room temperature for 2 hours
  2. customThe solvent was removed in vacuo and purification of the crude product by chromatography on silica eluting with iso-hexane

Sources & evidence

ORD record
ord-39f637f131d44e1d94484a259da39e8c
Source dataset
uspto-grants-2016_06
Patent number
US09365552B2

Reaction notes

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