Dimethylformamide → HCID 12018479, compound

Temperature

65 °C

5-Methylthiosalicylaldehyde (Step 1) (2.516 g, 14.96 mmole) was added to dimethylformamide (3.5 mL), potassium carbonate (2.27 g, 16.45 mmole) and ethyl 4,4,4-trifluorocrotonate (3.3 mL, 3.8 g, 22.4 mmole). The mixture was heated to 65° C. for 3 h. The reaction was cooled to room temperature, poured into H2O (50 mL), and extracted with diethyl ether (2×75 mL). The combined ethereal phases were washed with aqueous NaHCO3 solution (3×50 mL), aqueous 2 N HCl solution (3×50 mL), and brine (3×50 mL), dried over MgSO4, filtered, diluted with isooctane and partially concentrated in vacuo causing the precipitation of the ethyl ester (2.863 g, 60%) as a yellow powder: mp 87.8–89.6° C. This ester was of suitable purity to use without further purification.

1. temperatureThe reaction was cooled to room temperature
2. extractionextracted with diethyl ether (2×75 mL)
3. washThe combined ethereal phases were washed with aqueous NaHCO3 solution (3×50 mL), aqueous 2 N HCl solution (3×50 mL), and brine (3×50 mL)
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. additiondiluted with isooctane
7. concentrationpartially concentrated in vacuo
8. customthe precipitation of the ethyl ester (2.863 g, 60%) as a yellow powder
9. customto use without further purification

ORD record

ord-5ad0e1a1e577467dbd18ea6c6dd7bd63

Source dataset

uspto-grants-2006_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07138411B2