Sodium Chloride → HCID 178490111, compound

Participants

Reaction Conditions

Reaction Steps

350 mg (1.08 mmol) of (rac.)-4-(4-chloro-3-methoxyphenyl)-2-hydroxy-2-(trifluoromethyl)-pentanal is mixed in 5.8 ml of o-xylene with 190.9 mg (1.08 mmol) of 5-amino-8-fluoro-2-methylquinazoline. After 0.64 ml (2.16) titanium(IV) isopropylate is added, it is refluxed for three hours (bath temperature 120° C.). After cooling, the batch is added to saturated sodium chloride solution and stirred vigorously for 20 minutes. After 2× extraction with ethyl acetate, the combined organic extracts are washed with brine. After drying on sodium sulfate, and after the desiccant is suctioned off and the solvent is spun off, the residue is chromatographed on silica gel (mobile solvent ethyl acetate/hexane). 327.5 mg (62.8%) of the desired imine is isolated.

Provenance & Evidence