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Ammonium Chloride → (3,5-Difluoropyridin-2-YL)methanol

HRID 516979
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 516979
C([O:3][C:4]([C:6]1[C:11]([F:12])=[CH:10][C:9]([F:13])=[CH:8][N:7]=1)=O)C.[BH4-].[Na+].[Cl-].[NH4+]>C(O)C>[F:12][C:11]1[C:6]([CH2:4][OH:3])=[N:7][CH:8]=[C:9]([F:13])[CH:10]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 46311358Ethyl 3,5-difluoropyridine-2-carboxylate

Produkt 1

HCID 53414314(3,5-Difluoropyridin-2-YL)methanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 3,5-difluoro-pyridine-2-carboxylic acid ethyl ester of part A (2.5 g, 12.6 mmol) in ethanol (10 mL), cooled using an ice water bath, was added sodium borohydride (1.43 g, 37.8 mmol) in a portion wise manner. The solution was stirred at 0° C. for thirty minutes and at ambient temperature for 2 h. The reaction was returned to 0° C. and saturated ammonium chloride was added dropwise. The solvent was removed in vacuo and the resulting residue was partitioned between ethyl acetate and water. The organic layer was washed with saturated ammonium chloride, water and brine, and dried over magnesium sulfate. The slurry was filtered and concentrated to provide the alcohol as a yellow oil (1.8 g): MS (ES) m/e 146 (M+H).

Aufarbeitung

  1. customwas returned to 0° C.
  2. customThe solvent was removed in vacuo
  3. customthe resulting residue was partitioned between ethyl acetate and water
  4. washThe organic layer was washed with saturated ammonium chloride, water and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationThe slurry was filtered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-777de6ad333744ed95c335ee23cc25e4
Quelldatensatz
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09115089B2

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