Reaktion #90357

Reaktionsgleichung

1-(2-chloropyridin-3-yl)ethanol

isopropanol

NaHCO3

→

1-(2-chloropyridin-3-yl)ethanone

Ausbeute 77.0%

Lösungsmittel

acetone

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe solution was filtered through a bed of Celite
2. 2
   WaschenThe solids were washed by DCM
3. 3
   SonstigeThe organic phase of the filtrate was separated
4. 4
   Extraktionthe aqueous phase extracted with DCM (2×50 mL)
5. 5
   TrocknenThe combined organic layers were dried over MgSO4
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated under reduced pressure

Vorschrift

To a solution of 1-(2-chloropyridin-3-yl)ethanol (II) in dry acetone at -30° C. under nitrogen was added in portions chromium (VI) oxide (1.80 g, 18 mmol). The solution was further stirred 15 min at −30° C. and allowed to warm to room temperature. The solution was stirred for 3 h at room temperature before adding isopropanol (10 mL). The solution was made alkaline by slowly adding a saturated NaHCO3 solution. The solution was filtered through a bed of Celite. The solids were washed by DCM. The organic phase of the filtrate was separated and the aqueous phase extracted with DCM (2×50 mL). The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure to yield 1-(2-chloropyridin-3-yl)ethanone (III) as a brown liquid (0.72 g, 4.63 mmol, 77% yield). 1H NMR (CDCl3) δ ppm 2.71 (s, 3H), 7.35 (dd, J=7.63, 4.80 Hz, 1H), 7.91 (dd, J=7.54, 1.88 Hz, 1H), 8.55 (dd, J=4.71, 1.88 Hz, 1H).

Quelle