HCID 10988378, compound → HCID 86736405, compound

Participants

Reaction Steps

A suspension of 1.02 g (2.21 mmol) of product from Example 21 in 22 ml of dry tetrahydrofuran is stirred under argon with cooling to -78° and 1.24 ml (2.44 mmol) of a 1.97M n-butyllithium in hexane solution is added. The mixture is stirred for 30 minutes at -78° while 0.66 g (2.75 mmol) of benzhydryl glyoxylate in 20 ml of toluene is dried by distilling off 12 ml of the toluene. The remaining solution is added to the reaction mixture. The resulting mixture is stirred at -78° for 1 hour and then is warmed in an ice bath to 0° for 10 minutes. The reaction is quenched by pouring into cold aqueous NaH2PO4. The mixture is extracted with ethyl acetate and the combined extracts are washed with saline. The dried solution is evaporated and the residue is taken up in carbon tetrachloride and then hexane is added to precipitate the product, 15 g (97%).

Provenance & Evidence