Sodium borohydride → (5-(4-Chlorophenyl)pyridin-3-yl)methanol

HRID 33533Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 33533
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)[CH:7]=[N:6][CH:5]=1.[BH4-].[Na+]>C(O)C>[Cl:16][C:13]1[CH:12]=[CH:11][C:10]([C:8]2[CH:9]=[C:4]([CH2:3][OH:2])[CH:5]=[N:6][CH:7]=2)=[CH:15][CH:14]=1

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 20099851Methyl 5-(4-chlorophenyl)nicotinate

Produkt 1

HCID 24729853(5-(4-Chlorophenyl)pyridin-3-yl)methanolAusbeute 68,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A solution of 900 mg (3.49 mmol) 5-(4-Chloro-phenyl)-nicotinic acid methyl ester in 30.0 ml Ethanol was treated at room temperature (r. t.) with 264 mg (69.9 mmol) of sodium borohydride. The mixture was stirred for two days at 50° C. Then it was poured on ice and extracted tree times with ethyl acetate. The combined organic phases were washed with water, dried (sodium sulphate) and evaporated. Chromatography on silica (eluent: ethyl acetate/methanol 6:1) gave 522 mg (67%) of [5-(4-Chloro-phenyl)-pyridin-3-yl]-methanol.

Aufarbeitung

  1. additionThen it was poured on ice
  2. extractionextracted tree times with ethyl acetate
  3. washThe combined organic phases were washed with water
  4. dry with materialdried (sodium sulphate)
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-f884a7a13b014bd7be0032f745530dc0
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07429605B2

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