Phosphorus oxychloride → HCID 104367310, compound

To 8 mL dimethylformamide at room temperature was added phosphorous oxychloride (4.0 mL, 43.33 mmol) dropwise. After stirring for 10 minutes at room temperature, 2-(3,3,3-trifluoropropoxyl)thiophene (1.70 g, 8.67 mmol) as a solution in 8 mL dimethylformamide. The resulting solution was heated to 100° C. for 15 minutes. After cooling to room temperature, the reaction mixture was poured into 100 mL of ice-water and stirred vigorously for 5 minutes. Sodium bicarbonate (11 g) was added carefully and the mixture stirred until homogeneous. Organics were extracted with ether (3×100 mL), washed with water (3×50 mL), brine (50 mL), dried over magnesium sulfate, filtered and concentrated. The crude residue was subjected to chromatography on silica gel with gradient elution (0-20% ethyl acetate in hexanes) to give 5-(3,3,3-trifluoropropoxyl)thiophene-2-carbaldehyde (761 mg, 39%) as an off-white solid. Used without further characterization.

1. temperatureThe resulting solution was heated to 100° C. for 15 minutes
2. temperatureAfter cooling to room temperature
3. stirringstirred vigorously for 5 minutes
4. stirringthe mixture stirred until homogeneous
5. extractionOrganics were extracted with ether (3×100 mL)
6. washwashed with water (3×50 mL), brine (50 mL)
7. dry with materialdried over magnesium sulfate
8. filtrationfiltered
9. concentrationconcentrated
10. washThe crude residue was subjected to chromatography on silica gel with gradient elution (0-20% ethyl acetate in hexanes)

ORD record

ord-f1ac0715e6d34eca90bbe66664fc3622

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09315495B2