Hydrochloric Acid → HCID 86134675, compound

Temperature

-78 °C

To a solution of 2-ethoxythiophene (355 mg, 2.77 mmol) in 14 mL of 9:1 tetrahydrofuran/hexamethylphosphoramide under argon at −78° C. was added n-butyllithium (1.22 mL, 2.5 M in hexanes) dropwise over 5 minutes. After stirring at −78° C. for 20 minutes, dimethylformamide (1.07 mL, 13.9 mmol) was added in a single portion and the reaction mixture allowed to warm to room temperature while stirring, before being poured into 60 mL of 1 N hydrochloric acid. Organics were extracted with 1:1 ether/hexanes (2×75 mL), washed with 1 N hydrochloric acid (2×40 mL), water (40 mL) and brine, dried over magnesium sulfate, filtered and concentrated. The crude residue was subjected to chromatography on silica gel with gradient elution (5-7% ethyl acetate in hexanes) to give 5-ethoxy-2-thiophenecarbaldehyde (216 mg, 49%). Used without further characterization.

1. temperatureto warm to room temperature
2. stirringwhile stirring
3. extractionOrganics were extracted with 1:1 ether/hexanes (2×75 mL)
4. washwashed with 1 N hydrochloric acid (2×40 mL), water (40 mL) and brine
5. dry with materialdried over magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated
8. washThe crude residue was subjected to chromatography on silica gel with gradient elution (5-7% ethyl acetate in hexanes)

ORD record

ord-23c5141826754cf1a108b98ce0ad2976

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09315495B2