Dimethyl Sulfoxide → HCID 21883599, Verbindung

Temperatur

80 °C

A stirred solution of the dialdehyde (Step 2) (1.13 g, 6.14 mmol), dimethyl sulfoxide (6 mL), ethyl 4,4,4-trifluorocrotonate (1.37 mL, 1.55 g, 9.21 mmoL) and triethylamine (1.71 mL, 1.24 g, 12.28 mmol) in a round bottom flask fitted with condenser was heated to 80° C. for 8 h. Upon cooling to room temperature the reaction was diluted with diethyl ether (100 mL) and the resulting mixture washed with aqueous sodium bicarbonate solution (3×75 mL), 1 N HCl solution (3×70 mL), and brine (1×75 mL), dried over MgSO4, filtered and concentrated in vacuo yielding a tan powder. This powder was taken up in hot hexane-ethyl acetate and filtered to remove insoluble matter. Upon cooling of the filtrate, crystallization followed by vacuum filtration yielded the desired ester as tan crystals (0.726 g, 35%): mp 118.1–119.7° C. This material was of suitable purity to use without further purification.

1. temperatureUpon cooling to room temperature the reaction
2. washthe resulting mixture washed with aqueous sodium bicarbonate solution (3×75 mL), 1 N HCl solution (3×70 mL), and brine (1×75 mL)
3. dry with materialdried over MgSO4
4. filtrationfiltered
5. concentrationconcentrated in vacuo
6. customyielding a tan powder
7. filtrationfiltered
8. customto remove insoluble matter
9. temperatureUpon cooling of the filtrate, crystallization
10. filtrationfollowed by vacuum filtration

ORD-Eintrag

ord-b83320cb706b45c3823c139ca43ab160

Quelldatensatz

uspto-grants-2006_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07138411B2