theorganiclayerwaswashedwith7%H3PO4solution(13kg)andthenwith4wt%H3PO4solution(10.5kg).Theorganiclayerwastestedtoensurethelevelof8(≤20μg/mL).Theorganiclayerwaswashedwith2%NaClsolution(16kg)andaNaClandNaHCO3solution(1.7kgofNaCl。

yield98%).图片J.Med.Chem.EuropeanJournalofMedicinalChemistryThe2-hydroxy-1，2，3，4-tetrahydronaphthalene(65)(2.82g，19.1mmol)wasdissolvedindrypyridine。

extractedwithEt2O.TheorganicphasewasdriedoverNa2SO4，concentrated.Aflashchromatographydeliveredthepurecompound13(2.0g，69%)asayellowoil.图片JournaloftheChemicalSocietyAsolutionofthetestosteroneester(0.5g)andtetrabutylammoniumbromide(2.1g.。