Hydrochloric Acid → HCID 118230555, compound

To a solution of 5-(3-hydroxypropyl)thiophene-2-carbaldehyde (Example 58.1; 70 mg, 0.41 mmol) in 1 mL anhydrous tetrahydrofuran under argon at room temperature was added hexanes-rinsed sodium hydride (17 mg of 60% dispersion in oil, 0.45 mmol) as a slurry in 1 mL anhydrous tetrahydrofuran. The resulting suspension was stirred for 15 minutes at room temperature. Methyl iodide (35 μL, 0.57 mmol) was added and the resulting mixture stirred for 2 h at room temperature. The reaction mixture was poured into 30 mL of 0.2 N hydrochloric acid. Organics were extracted with ether (2×30 mL), washed with 5% sodium bisulfite solution, dried over magnesium sulfate, filtered and concentrated. The crude residue was subjected to chromatography on silica gel with gradient elution (8-12% ethyl acetate in hexanes) to give 5-(3-methoxypropyl)thiophene-2-carbaldehyde (17 mg, 23%) as an oil. Used without further characterization.

1. stirringthe resulting mixture stirred for 2 h at room temperature
2. extractionOrganics were extracted with ether (2×30 mL)
3. washwashed with 5% sodium bisulfite solution
4. dry with materialdried over magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated
7. washThe crude residue was subjected to chromatography on silica gel with gradient elution (8-12% ethyl acetate in hexanes)

ORD record

ord-ca82f90c50664b909314e4de7a5bd10c

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09315495B2