Hydrochloric Acid → HCID 54303603, compound

A mixture was prepared of 5.14 g. (0.02 mole) of 4-(dimethylamino)-3-(α,α,α-trifluoro-m-tolyl)-3-buten-2-one and 75 ml. of dry tetrahydrofuran and there was added dropwise thereto an equivalent amount of n-butyllithium in hexane while maintaining the temperature of the reaction mixture at about -20° C. After the addition was complete the mixture was stirred for about 1 hour at a temperature of about -20° to -30° C. The reaction mixture was then allowed to warm to room temperature and 25 ml. of 1 N HCl was added and the mixture was concentrated in vacuo. The residual dark oil was taken up in 100 ml. of ether and washed with 2×50 ml. of water and dried over anhydrous magnesium sulfate. The drying agent was filtered off and the filtrate was concentrated in vacuo to give a dark oil. This oil was chromatographed over silica gel using ether as a solvent and eluent and the product was finally purified by molecular distillation. The product was identified by elemental analyses as 3-(α,α,α-trifluoro-m-tolyl)-3-octen-2-one. It weighed 4.5 g. (83% yield).

1. customA mixture was prepared of 5.14 g
2. additionAfter the addition
3. concentrationthe mixture was concentrated in vacuo
4. washof ether and washed with 2×50 ml
5. dry with materialof water and dried over anhydrous magnesium sulfate
6. filtrationThe drying agent was filtered off
7. concentrationthe filtrate was concentrated in vacuo
8. customto give a dark oil
9. customThis oil was chromatographed over silica gel
10. distillationeluent and the product was finally purified by molecular distillation

ORD record

ord-55c73c329de1432483dafe0418f073af

Source dataset

uspto-grants-1979_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04175087