Pyridine → HCID 66787451, compound

Temperature

0 °C

A mixture of trifluoromethylphenylketone [C.A.S. 434-45-7] (5 g, 28.71 mmol) and ethyl cyanoacetate [C.A.S. 105-56-6] (3.61 mL, 31.58 mmol) in DCM (100 mL) was flushed with nitrogen, then cooled to 0° C. and maintained under a nitrogen atmosphere. Neat titanium(IV) chloride (6.79 mL, 60.30 mmol) was added dropwise, the reaction mixture was stirred for 10 min at 0° C. and then pyridine (1.5 mL) was added dropwise. When the addition was complete, the ice bath was removed, the reaction was stirred for 30 min at r.t., additional pyridine was added (5 mL) and the reaction mixture was stirred for a further 20 h at r.t. The mixture was then diluted in DCM (100 mL) and washed with HCl 2N (2×200 mL), water (300 mL) and brine (100 mL). The organic phase was evaporated to yield intermediate compound D42 (4.8 g, 61%) as a mixture of E/Z isomers, as a colourless oil which was used without further purification.

1. customwas flushed with nitrogen
2. temperaturemaintained under a nitrogen atmosphere
3. additionWhen the addition
4. customthe ice bath was removed
5. stirringthe reaction was stirred for 30 min at r.t.
6. additionadditional pyridine was added (5 mL)
7. stirringthe reaction mixture was stirred for a further 20 h at r.t
8. additionThe mixture was then diluted in DCM (100 mL)
9. washwashed with HCl 2N (2×200 mL), water (300 mL) and brine (100 mL)
10. customThe organic phase was evaporated
11. customto yield intermediate compound D42 (4.8 g, 61%)
12. additionas a mixture of E/Z isomers
13. customas a colourless oil which was used without further purification

ORD record

ord-bb6fc6c56f564c52a5d31dfaeb495978

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09226930B2