Triethylamine → HCID 90442040, compound

Temperature

110 °C

Into a 10-mL sealed tube (1 atm) purged and maintained with an inert atmosphere of nitrogen, was placed 1-bromo-4-methoxy-3-methyl-2-(trifluoromethyl)benzene (300 mg, 1.12 mmol, 1.00 equiv), ethyl prop-2-enoate (560 mg, 5.59 mmol, 5.02 equiv), P(Tol)3 (61 mg, 0.20 mmol, 0.18 equiv), Pd(OAc)2 (30 mg, 0.13 mmol, 0.12 equiv), triethylamine (566 mg, 5.59 mmol, 5.02 equiv), N,N-dimethylformamide (2.0 mL). The resulting solution was stirred overnight at 110° C. in an oil bath. The reaction progress was monitored by GCMS. The reaction was then quenched by the addition of 10 mL of water. The resulting solution was extracted with 3×15 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 2×20 mL of H2O. The mixture was dried over anhydrous sodium sulfate. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:6). This resulted in 0.16 g (50%) of ethyl (2E)-3-[4-methoxy-3-methyl-2-(trifluoromethyl)phenyl]prop-2-enoate as a yellow solid.

1. customInto a 10-mL sealed tube (1 atm)
2. custompurged
3. temperaturemaintained with an inert atmosphere of nitrogen
4. customThe reaction was then quenched by the addition of 10 mL of water
5. extractionThe resulting solution was extracted with 3×15 mL of ethyl acetate
6. washThe resulting mixture was washed with 2×20 mL of H2O
7. dry with materialThe mixture was dried over anhydrous sodium sulfate
8. customThis resulted in 0.16 g (50%) of ethyl (2E)-3-[4-methoxy-3-methyl-2-(trifluoromethyl)phenyl]prop-2-enoate as a yellow solid

ORD record

ord-60242fc4bdc848518124669d7e17f858

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09067898B1