Facile synthesis of trifluoromethyl carbinols and trifluoromethyl-α,β-unsaturated ketones from the new CF3CHO synthetic equivalent, 1,1-bis(dimethylamino)-2,2,2-trifluoroethane

✍ Scribed by Yuelian Xu; William R. Dolbier Jr.

• Publisher: Elsevier Science
• Year: 1998
• Tongue: French
• Weight: 207 KB
• Volume: 39
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(98)02106-6

✦ Synopsis

1,1-Bis(dimethylamino)-2,2,2-trifluoroethane is an excellent synthetic building-block replacement for trifluoroacetaldehyde in condensation reactions with ketones using 36% aqueous HCI catalysis. Moderate to good yields (43-68%) of trifluoromethyl carbinols are obtained with symmetric and unsymmetric methyl ketones, with the latter undergoing reaction mainly at the methyl group. Its reactions with silyl enol ethers under anhydrous conditions, catalyzed by ZnI2, lead directly to trifluoromethyl-eq[~-unsaturated ketones.