Benzyl Alcohol → 2-(Benzyloxy)-6-fluoropyridine

HRID 1255520Notizen

Reaktionsgleichung

[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12](F)[N:11]=1.[H-].[Na+].O>O1CCCC1>[CH2:1]([O:8][C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([F:9])[N:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

An oven-dried 3-neck 2 L round bottom flask under nitrogen was charged with benzyl alcohol (9.04 ml, 87 mmol) and tetrahydrofuran (75 ml). Attached an addition funnel containing a solution of 2,6-difluoropyridine (10.00 g, 87 mmol) in tetrahydrofuran (30 ml). Sodium hydride (3.82 g, 96 mmol) was added in small portions with stirring. Heated in a 50° C. oil bath for 45 minutes; cooled to room temperature. Added contents of addition funnel dropwise. After 18 hours poured into water. Extracted three times with ethyl acetate, washed combined organic portions with brine, dried with anhydrous magnesium sulfate, filtered and rotary evaporated filtrate. The crude product was subjected to flash column chromatography eluting with hexane. Evaporation of fractions gave the title compound as a colorless oil. (17.70 g, 87 mmol, 100% yield). LCMS (ES+) m/z 204.3 (M+H)+.

Aufarbeitung

temperaturecooled to room temperature
additionAdded contents of addition funnel dropwise
extractionExtracted three times with ethyl acetate
washwashed
dry with materialdried with anhydrous magnesium sulfate
filtrationfiltered
washeluting with hexane
customEvaporation of fractions

Quellen und Nachweise

ORD-Eintrag: ord-21fe216a09f04447a526fb20d25626f7
Quelldatensatz: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08461107B2

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