Potassium Hydroxide → HCID 67598476, compound

To a suspension of the triflate salt obtained in Example 23 (2.34 g, 5.38 mmol) in chloroform (500 mL) was added aqueous 5% KOH. The chloroform layer was separated and the aqueous layer was extracted with chloroform (5×350 mL). The ensuing emulsion was separated from the aqueous layer. Anhydrous Na2CO3 was added to the emulsion until it obtained a paste-like consistency. The aqueous layer was repeatedly extracted with chloroform until the aqueous layer was no longer purple. The Na2CO3 paste was ground with a mortar and pestle and exhaustively extracted with chloroform. All chloroform extracts were combined, dried over anhydrous Na2CO3, filtered and concentrated. The resulting solid was resuspended in chloroform (800 mL), solid anhydrous Na2CO3 was added to the suspension (100 g), and the mixture was sonicated and then concentrated. The resulting solid was poured onto a basic alumina column, eluted sequentially with chloroform (1000 mL), EtOAc-chloroform (1:9, 1000 mL), EtOAc-chloroform (1.5:8.5, 1000 mL), EtOAc-chloroform (2.5:7.5, 1000 mL), and EtOAc-chloroform (3.5:6.5, 1000 mL) to remove the impurities. Elution with 4% methanol in chloroform afforded 1.48 g (96.7%) of the title compound as a purple solid.

1. customThe chloroform layer was separated
2. extractionthe aqueous layer was extracted with chloroform (5×350 mL)
3. customThe ensuing emulsion was separated from the aqueous layer
4. additionAnhydrous Na2CO3 was added to the emulsion until it
5. customobtained a paste-like consistency
6. extractionThe aqueous layer was repeatedly extracted with chloroform until the aqueous layer
7. extractionexhaustively extracted with chloroform
8. dry with materialdried over anhydrous Na2CO3
9. filtrationfiltered
10. concentrationconcentrated
11. additionsolid anhydrous Na2CO3 was added to the suspension (100 g)
12. customthe mixture was sonicated
13. concentrationconcentrated
14. additionThe resulting solid was poured onto a basic alumina column
15. washeluted sequentially with chloroform (1000 mL), EtOAc-chloroform (1:9, 1000 mL), EtOAc-chloroform (1.5:8.5, 1000 mL), EtOAc-chloroform (2.5:7.5, 1000 mL), and EtOAc-chloroform (3.5:6.5, 1000 mL)
16. customto remove the impurities
17. washElution with 4% methanol in chloroform

ORD record

ord-2a0b2aa8318f4d09a6ffeff19603a9eb

Source dataset

uspto-grants-1997_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05681958