Reaktion #7391

Reaktionsgleichung

4-chloro-3-hydroxy-benzaldehyde

tert-butyldimethylsilyl chloride

triethylamine

→

title compound

3-{[tert-Butyl(dimethyl)silyl]oxy}-4-chlorobenzaldehyde

Lösungsmittel

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe mixture was quenched with saturated aqueous sodium bicarbonate
2. 2
   Extraktionextracted with diethyl ether
3. 3
   EinengenThe combined organic extracts were concentrated under reduced pressure
4. 4
   Sonstigeto give an oil which
5. 5
   Sonstigewas purified
6. 6
   WaschenSPE (silica, eluting with cyclohexane followed by 10% to 30% ethyl acetate-cyclohexane)

Vorschrift

A mixture of 4-chloro-3-hydroxy-benzaldehyde* (0.354 g), 4-N,N-dimethylaminopyridine (0.028 g), tert-butyldimethylsilyl chloride (0.409 g) and triethylamine (0.473 ml) in DCM (15 ml) was stirred at room temperature under nitrogen for 19 h. The mixture was quenched with saturated aqueous sodium bicarbonate and extracted with diethyl ether. The combined organic extracts were concentrated under reduced pressure to give an oil which was purified using SPE (silica, eluting with cyclohexane followed by 10% to 30% ethyl acetate-cyclohexane) to give the title compound (0.42 g) as an oil. *Kelley, J; Linn, J; Selway, J. W. T., J. Med. Chem. (1989), 32(8), 1757–63.

Quelle