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

HRID 33521

Reaktionsgleichung

C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)[CH:7]=[N:6][CH:5]=1.[BH4-].[Na+]>C(O)C>[F:18][C:16]([F:17])([F:19])[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

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

A solution of 335 mg (1.17 mmol) 5-(4-Trifluoromethyl-phenyl)-nicotinic acid methyl ester in 10.0 ml ethanol was treated at room temperature (r. t.) with 44 mg (1.17 mmol) of sodium borohydride. The mixture stirred 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 5:1) gave 195 mg (64%) of [5-(4-Trifluoromethyl-phenyl)-pyridin-3-yl]-methanol.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag: ord-e9070980bb7a4af4980a657c08557dec
Quelldatensatz: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07429605B2

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