Réaction #7391

Équation de réaction

4-chloro-3-hydroxy-benzaldehyde

tert-butyldimethylsilyl chloride

triethylamine

→

title compound

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

Solvants

DCM

Conditions de réaction

Traitement

1. 1
   AutreThe mixture was quenched with saturated aqueous sodium bicarbonate
2. 2
   Extractionextracted with diethyl ether
3. 3
   ConcentrationThe combined organic extracts were concentrated under reduced pressure
4. 4
   Autreto give an oil which
5. 5
   Autrewas purified
6. 6
   LavageSPE (silica, eluting with cyclohexane followed by 10% to 30% ethyl acetate-cyclohexane)

Mode opératoire

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.

Source