Lithium Hydroxide → 5-(But-2-ynyloxy)picolinic acid

HRID 627727

Reaktionsgleichung

Reaktionsgleichung von HRID 627727
[CH2:1]([O:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]([O-:14])=[O:13])=[N:10][CH:11]=1)[C:2]#[C:3][CH3:4].[OH-].[Li+]>CO.O1CCOCC1.O>[CH2:1]([O:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]([OH:14])=[O:13])=[N:10][CH:11]=1)[C:2]#[C:3][CH3:4]

Komponenten

6

Edukt 2

HCID 3939Lithium HydroxideHCID 867281605-(But-2-yn-1-yloxy)picolinate

Produkt 1

HCID 679795075-(But-2-ynyloxy)picolinic acidAusbeute 83,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of 5-(but-2-yn-1-yloxy)picolinate (72 mg, 0.35 mmol) in methanol (1 ml), dioxane (1 ml) and water (0.1 ml) was added lithium hydroxide (31 mg, 1.3 mmol). The reactions were stirred at ambient temperature for 2 h. The solvents were removed in vacuo. The residue from the reaction was triturated with 0.5 mL 1 N aqueous HCl. The tan precipitate was collected by vacuum filtration, washed with water, and dried in vacuo to generate 5-(but-2-yn-1-yloxy)picolinic acid (56 mg, 0.293 mmol, 83% yield) as a tan powder. LC/MS (ESI+) m/z=192 (M+H).

Aufarbeitung

  1. customThe solvents were removed in vacuo
  2. customThe residue from the reaction was triturated with 0.5 mL 1 N aqueous HCl
  3. filtrationThe tan precipitate was collected by vacuum filtration
  4. washwashed with water
  5. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-bcd9446daf514f959cb0506703fd5fa0
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309263B2

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