Diethyl Ether → HCID 59949024, compound

Temperature

0 °C

To a solution of the product from Example 15B in CH2Cl2 was added triethylamine (6.6 mL), 2,4,6-triisopropylbenzenesulfonyl chloride (11.5 g), and DMAP (0.386 g). After 14 hours, the reaction was diluted with ether, chilled to 0° C., filtered through celite, and concentrated. The residue was dissolved in ethanol (100 mL) and 1M NaOH (32 mL) was added. After 30 minutes, the reaction was carefully concentrated, diluted with water (100 mL), and extracted into ether (3×50 mL). The organic extracts were washed with brine (20 mL), dried (MgSO4), filtered, and concentrated to provide a colorless aromatic oil which was purified first by passage through a plug of silica gel eluting with 5% EtOAc/hexanes, then by bulb-to-bulb distillation under reduced pressure to provide 3.3 g (75%) of the title compound as a colorless aromatic oil.

1. filtrationfiltered through celite
2. concentrationconcentrated
3. dissolutionThe residue was dissolved in ethanol (100 mL)
4. addition1M NaOH (32 mL) was added
5. waitAfter 30 minutes
6. concentrationthe reaction was carefully concentrated
7. additiondiluted with water (100 mL)
8. extractionextracted into ether (3×50 mL)
9. washThe organic extracts were washed with brine (20 mL)
10. dry with materialdried (MgSO4)
11. filtrationfiltered
12. concentrationconcentrated
13. customto provide a colorless aromatic oil which
14. customwas purified first by passage through a plug of silica gel eluting with 5% EtOAc/hexanes
15. distillationby bulb-to-bulb distillation under reduced pressure

ORD record

ord-5d331000fddf4343a2eb4538995c89c0

Source dataset

uspto-grants-2001_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06277871B1