Hydrochloric Acid → HCID 70926934, compound

In methylene chloride (16.2 mL), 3,4-dihydro-2H-pyran (10.6 mL) was dissolved. To the solution, a solution of 4M hydrogen chloride in 1,4-dioxane (31.1 μL) was added and (1S)-4-bromo-2,3-dihydro-1H-inden-1-ol (10.0 g) that was commercially available or could be obtained by a known method was added. The resultant reaction mixture was stirred at room temperature for 3 hours. To the reaction mixture, a saturated aqueous sodium hydrogen carbonate solution (60 mL) was added and extracted with methylene chloride (60 mL). The organic phase was washed with brine (60 mL) and dried over anhydrous sodium sulfate. From the organic phase, the solvent was removed by evaporation under reduced pressure and the resultant residue was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=95:5). From the eluted solution, the solvent was removed by evaporation under reduced pressure to give the title compound (15 g).

1. customcould be obtained by a known method
2. additionwas added
3. customThe resultant reaction mixture
4. extractionextracted with methylene chloride (60 mL)
5. washThe organic phase was washed with brine (60 mL)
6. dry with materialdried over anhydrous sodium sulfate
7. customFrom the organic phase, the solvent was removed by evaporation under reduced pressure
8. customthe resultant residue was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=95:5)
9. customFrom the eluted solution, the solvent was removed by evaporation under reduced pressure

ORD record

ord-3cbb6ef7f0154f5b95a7384cfb1a5744

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09040525B2