Reaktionsgleichung
Cl[C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].[OH-].[K+].[O:17]1[CH2:22][CH2:21][CH:20]([CH2:23][OH:24])[CH2:19][CH2:18]1>CS(C)=O>[O:17]1[CH2:22][CH2:21][CH:20]([CH2:23][O:24][C:2]2[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][C:3]=2[C:11]([F:14])([F:13])[F:12])[CH2:19][CH2:18]1Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
6-Chloro-5-(trifluoromethyl)picolinic acid (330 mg, 1.46 mmol) and powdered potassium hydroxide (328 mg, 5.85 mmol) were dissolved in DMSO (9 mL). The solution was stirred for 15 min. at ambient temperature. (Tetrahydro-2H-pyran-4-yl)methanol (170 mg, 170 μL, 1.46 mmol; CAN 14774-37-9) was added. The mixture was stirred for 1 d at ambient temp., poured onto ice water/brine/1N HCl (75 mL) and extracted with EtOAc (2×150 mL). The combined extracts were washed with ice water/brine (75 mL), dried over Na2SO4. The solvent was removed under reduced pressure to give the title compound as a grey solid (385 mg, 86%) which was used in the next step without further purification. MS: 304.0 [M−H]−.
Aufarbeitung
- stirringThe mixture was stirred for 1 d at ambient temp.
- additionpoured onto ice water/brine/1N HCl (75 mL)
- extractionextracted with EtOAc (2×150 mL)
- washThe combined extracts were washed with ice water/brine (75 mL)
- dry with materialdried over Na2SO4
- customThe solvent was removed under reduced pressure
Quellen und Nachweise
- ORD-Eintrag
- ord-ed82bb8ba16a4b558e0b9e9a5bd2b406
- Quelldatensatz
- uspto-grants-2016_04
- Patentnummer
- US09321727B2
Verknüpfte Notizen
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