Potassium Carbonate → 4'-[(4-hydroxytetrahydro-2H-thiopyran-4-yl)methoxy]-2',6'-dimethylbiphenyl-3-carbaldehyde

To a solution of 1-oxa-6-thiaspiro[2.5]octane (6.33 g, 48.6 mmol) and 4′-hydroxy-2′,6′-dimethylbiphenyl-3-carbaldehyde (10.0 g, 44.2 mmol) in N,N-dimethylformamide (150 mL) was added potassium carbonate (6.11 g, 44.2 mmol) at room temperature with stirring and the mixture was stirred at 100° C. for 12 hrs. The reaction mixture was concentrated under reduced pressure. To the residue was added 1 M hydrochloric acid to neutralize the solution and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, concentrated under reduced pressure and crystallized by adding diisopropyl ether to the obtained oil. The crystals were collected by filtration to give the title compound (12.3 g, yield 78%) as colorless crystals.

1. stirringthe mixture was stirred at 100° C. for 12 hrs
2. concentrationThe reaction mixture was concentrated under reduced pressure
3. additionTo the residue was added 1 M hydrochloric acid
4. extractionthe mixture was extracted with ethyl acetate
5. dry with materialThe extract was dried over anhydrous sodium sulfate
6. concentrationconcentrated under reduced pressure
7. customcrystallized
8. additionby adding diisopropyl ether to the obtained oil
9. filtrationThe crystals were collected by filtration

ORD record

ord-2780be9b2a004cf9a62fea5c16881bbe

Source dataset

uspto-grants-2008_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07456218B2