Pyridine → 1-(t-Butyldimethylsilyl)-4-(2-oxoethyl)-2-azetidinone

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Reaction Steps

Anhydrous CrO3 (1.94 g, 19.38 mmol) is added to a solution of anhydrous pyridine (3.07 g, 38.76 mmol) in anhydrous CH2Cl2 (50 ml). The resulting mixture is stirred at r.t. for 15 min. A solution of 1-(t-butyldimethylsilyl)-4-(2-hydroxyethyl)-2-azetidinone (0.74 g, 3.23 mmol) in anhydrous CH2Cl2 5 ml is added all at once. After stirring for 5 min, the CH2Cl2 solution is separated from a dark gummy precipitate which is washed with more CH2Cl2. The combined CH2Cl2 solution is evaporated under vacuum. The residue is taken up in ether filtered and washed with 5% NaHCO3, 5% HCl, 5% NaHCO3 and brine then dried and evaporated to give the aldehyde (0.543 g 74%).

Provenance & Evidence