Hydrochloric Acid → HCID 58042516, Verbindung

HRID 2048036Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2048036
[H-].[Na+].[F:3][C:4]1([F:10])[CH2:7][CH:6]([CH2:8][OH:9])[CH2:5]1.Cl[C:12]1[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][N:13]=1.Cl>C1COCC1>[Cl:18][C:17]1[C:12]([O:9][CH2:8][CH:6]2[CH2:7][C:4]([F:10])([F:3])[CH2:5]2)=[N:13][CH:14]=[CH:15][CH:16]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 169882,3-DichloropyridineHCID 24758Sodium hydrideHCID 45480377(3,3-Difluorocyclobutyl)methanol

Produkt 1

HCID 58042516HCID 58042516, VerbindungAusbeute 93,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Sodium hydride (60% dispersion in mineral oil, 1.017 g, 70.6 mmol) was suspended in THF (30.0 mL) and the reaction was cooled to 0° C. under nitrogen with an ice bath. (3,3-Difluorocyclobutyl)methanol (Preparation 2, 2.95 g, 24.2 mmol) in THF (30 mL) was added dropwise to the mixture maintaining the temperature at 0° C. After stirring for 30 minutes, 2,3-dichloropyridine (3.25 g, 22.0 mmol) was added and the suspension was heated to reflux for 16 hours. An aqueous solution of HCl (1.0M, 20 mL) was added and the reaction was extracted with EtOAc (2×100 mL). The combined organics were then dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (Biotage®, gradient of 0-50% EtOAc in heptane,) to afford the title compound (4.82 g, 85%):

Aufarbeitung

  1. temperaturemaintaining the temperature at 0° C
  2. temperaturethe suspension was heated
  3. temperatureto reflux for 16 hours
  4. extractionthe reaction was extracted with EtOAc (2×100 mL)
  5. dry with materialThe combined organics were then dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel chromatography (Biotage®, gradient of 0-50% EtOAc in heptane,)

Quellen und Nachweise

ORD-Eintrag
ord-d4de9b5ad40049fabe768125b309fc56
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08592629B2

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