Potassium Carbonate → HCID 86712700, compound

K2CO3 (0.210 g, 1.52 mmol) was added to a solution of methyl 2-(2-((triethylsilyl)ethynyl)-6-(trifluoromethyl)phenyl)acetate (A92) (0.175 g, 0.491 mmol) in MeOH (1 mL) and the mixture stirred for 10 minutes at room temperature. The resulting mixture was diluted with water (20 mL) and extracted with DCM (3×20 mL). The combined organic extracts were concentrated under reduced pressure and the residue dissolved in MeOH (1 mL). K2CO3 (0.204 g, 1.48 mmol) was added and the mixture stirred at room temperature for 30 minutes. The resulting mixture was diluted with water (20 mL) and extracted with DCM (3×20 mL) then the combined organic extracts were concentrated under reduced pressure. The residue was dissolved in MeOH (2 mL) to which K2CO3 (0.230 g, 1.66 mmol) was added and the resulting mixture stirred at room temperature for 30 minutes. Water (20 mL) was added and the mixture extracted with DCM (3×20 mL). The combined organic extracts were concentrated under reduced pressure to give the title compound A93 (0.113 g, 95%); 1H NMR (400 MHz, CDCl3) δ 7.71 (d, J=7.7 Hz, 1H), 7.67 (d, J=8.0 Hz, 1H), 7.38 (m, 1H), 4.08 (m, 2H), 3.70 (s, 3H), 3.35 (s, 1H).

1. extractionextracted with DCM (3×20 mL)
2. concentrationThe combined organic extracts were concentrated under reduced pressure
3. dissolutionthe residue dissolved in MeOH (1 mL)
4. stirringthe mixture stirred at room temperature for 30 minutes
5. extractionextracted with DCM (3×20 mL)
6. concentrationthe combined organic extracts were concentrated under reduced pressure
7. additionwas added
8. stirringthe resulting mixture stirred at room temperature for 30 minutes
9. extractionthe mixture extracted with DCM (3×20 mL)
10. concentrationThe combined organic extracts were concentrated under reduced pressure

ORD record

ord-3ecb3b9e5a7b4ce282d184289b52f0c8

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09266864B2