Isopropanol → 2-[(Propan-2-yl)oxy]thiophene

Temperature

90 °C

To a mixture of 10 mL anhydrous isopropanol and 5 mL anhydrous tetrahydrofuran under argon at room temperature was added sodium metal (350 mg, 15.22 mmol). The resulting mixture was stirred vigorously at 35° C. until all the sodium metal was consumed (ca. 20 minutes). Copper(I) iodide (386 mg, 2.03 mmol) and 2-iodothiophene (2.13 g, 10.14 mmol) were added and the resulting suspension heated to 90° C. and stirred vigorously for 16 h. After cooling to room temperature, 20 mL of 0.5 M potassium cyanide aqueous solution was added and the resulting mixture stirred for 30 minutes. Organics were extracted with hexanes (2×75 mL), washed with water (3×50 mL) and brine (50 mL), dried over magnesium sulfate, filtered and concentrated. The residue was subjected to chromatography on silica gel (100% hexanes) to give 2-isopropoxythiophene (250 mg, 16%). Used without further characterization.

1. customwas consumed (ca. 20 minutes)
2. temperatureAfter cooling to room temperature
3. stirringthe resulting mixture stirred for 30 minutes
4. extractionOrganics were extracted with hexanes (2×75 mL)
5. washwashed with water (3×50 mL) and brine (50 mL)
6. dry with materialdried over magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated

ORD record

ord-0b15eb8bc77b498188514a7e0b5c4649

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09315495B2