indium(III)chloride → 6,7-dihydro-4H-thieno[3,2-c]pyran

11.0 g of 2-[2-(2-methoxyethoxymethoxy)ethyl]thiophene obtained in Example 20 and 1.1 g of indium(III) chloride were added to 750 mL of acetonitrile, and the resulting mixture was refluxed for 5 hours. The reaction product solution was cooled to room temperature and concentrated by evaporation under reduced pressure. To the residue, 100 mL of water and 150 mL of n-hexane were added, and the resulting mixture was stirred for 5 minutes. Aqueous layer was discarded, and the organic layer was washed twice with 70 mL portions of water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was distilled under reduced pressure to obtain 2.9 g (yield of 41%) of the title compound, of which analysis data were the same as obtained in Example 14.

1. temperaturethe resulting mixture was refluxed for 5 hours
2. concentrationconcentrated by evaporation under reduced pressure
3. additionTo the residue, 100 mL of water and 150 mL of n-hexane were added
4. washthe organic layer was washed twice with 70 mL portions of water
5. dry with materialdried over anhydrous magnesium sulfate
6. concentrationconcentrated under reduced pressure
7. distillationThe residue was distilled under reduced pressure

ORD record

ord-2d05f5d189e2465a9bc18f9369ffa940

Source dataset

uspto-grants-2008_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07449580B2