Iodoethane → HCID 67205011, Verbindung

HRID 1894318Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1894318
[CH2:1]([O:3][C:4](=[O:16])[C:5]1[C:10]([OH:11])=[CH:9][C:8]([C:12]([CH3:15])([CH3:14])[CH3:13])=[N:7][CH:6]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:23](I)[CH3:24]>CN(C)C=O.O.[Cl-].[Na+].O>[CH2:1]([O:3][C:4](=[O:16])[C:5]1[C:10]([O:11][CH2:23][CH3:24])=[CH:9][C:8]([C:12]([CH3:15])([CH3:14])[CH3:13])=[N:7][CH:6]=1)[CH3:2]

Komponenten

7

Edukt 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 178469765HCID 178469765, Verbindung

Produkt 1

HCID 67205011HCID 67205011, VerbindungAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

6-tert-Butyl-4-hydroxy-nicotinic acid ethyl ester (110 mg, 0.5 mmol) was dissolved in dimethylformamide (6 mL). Potassium carbonate was added followed by dropwise addition of ethyl iodine (0.13 mL, 1.5 mmol). The reaction mixture was stirred at room temperature overnight. It was diluted with water and brine and extracted with diethyl ether (2×30 mL). Combined organics washed with brine/water, dried and concentrated to give 6-tert-butyl-4-ethoxy-nicotinic acid ethyl ester as viscous oil (100 mg, 80%). LR-MS: 251 [(M+H)+]

Aufarbeitung

  1. extractionextracted with diethyl ether (2×30 mL)
  2. washCombined organics washed with brine/water
  3. customdried
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-2607a40e64bd4ba6b10ccc5724155844
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08513239B2

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