Diethyl Ether → 3-(2-Methoxyethoxy)thiophene

Temperature

118 °C

Sodium metal (1.05 g, 45.8 mmol) cut into small pieces was added to 2-methoxyethanol (12 mL) at room temperature under nitrogen. The reaction was heated at 75° C. until all the sodium metal dissolved (about 45 min). 3-Bromothiophene (2.49 g, 15.3 mmol) and copper(1) bromide (0.22 g, 1.53 mmol) were added to the reaction mixture and the heat was increased to 118° C. for 1.5 h. The reaction was allowed to cool to room temperature and the mixture was poured into a mixture of brine and ether (1:1, 100 mL). Vigorous stirring caused an emulsion which was removed by filtration through celite washing the filter cake with ether (40 mL). The organic layer was separated and the aqueous layer extracted with ether (3×30 mL). The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and evaporated to dryness. The residue was purified by silica gel chromatography to afford 1.83 g of 3-(2-methoxyethoxy)thiophene (76% yield) as a clear liquid. 1H NMR (300 MHz, CDCl3) δ ppm 7.17 (dd, J=5.3, 3.2 Hz, 1H), 6.80 (dd, J=5.1, 1.5 Hz, 1H), 6.26 (dd, J=3, 1.5 Hz, 1H), 4.14-4.08 (m, 2H), 3.77-3.70 (m, 2H), 3.44 (s, 3H).

1. dissolutiondissolved (about 45 min)
2. temperatureto cool to room temperature
3. customwas removed by filtration through celite
4. washwashing the filter cake with ether (40 mL)
5. customThe organic layer was separated
6. extractionthe aqueous layer extracted with ether (3×30 mL)
7. washThe combined organic layers were washed with brine
8. dry with materialdried over magnesium sulfate
9. filtrationfiltered
10. customevaporated to dryness
11. customThe residue was purified by silica gel chromatography

ORD record

ord-d0124d72d6df4e8eab13b9892c2a0562

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07884107B2