Reaktion #806073

Reaktionsgleichung

sodium acetate

phosphoryl chloride

N-(2-oxotetrahydrothiophen-3-yl)acetamide

dimethylformamide

→

title compound

Ausbeute 18.0%

5-chlorothieno[3,2-b]pyridine-3-carbaldehyde

Ausbeute 18.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   ExtraktionThe solution was extracted by ethyl acetate 1000 ml
2. 2
   WaschenThe organic phase was washed with water 300 ml and brine 200 ml
3. 3
   TrocknenThen the organic phase was dried over magnesium sulfate
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated
6. 6
   SonstigeThe residue was crystallized by addition of ethyl acetate/ether (1:1) 200 ml
7. 7
   Filtrationfiltered
8. 8
   EinengenThe filtrate was concentrated

Vorschrift

To the solution of phosphoryl chloride 14.9 ml (160 mmol) in dimethylformamide 45 ml, N-(2-oxotetrahydrothiophen-3-yl)acetamide 12.74 g (80 mmol) was added portion wise and stirred at 90° C. for 2 hours. The reaction mixture was poured into ice water 400 ml and followed by addition of saturated sodium acetate 500 ml. The solution was extracted by ethyl acetate 1000 ml. The organic phase was washed with water 300 ml and brine 200 ml. Then the organic phase was dried over magnesium sulfate, filtered and concentrated. The residue was crystallized by addition of ethyl acetate/ether (1:1) 200 ml and filtered. The filtrate was concentrated to obtain the title compound 3.55 g (18%).

Quelle