反应详情

Ethyl 4-(tert-butyldimethylsilyloxy)-1-methylcyclohexanecarboxylate (Intermediate 66, 1.32 g, 4.39 mmol) was dissolved in THF (25 ml), to which tetrabutylammonium fluoride (TBAF, 1M solution in THF) (7.34 ml, 7.34 mmol) was added. The reaction mixture was stirred at room temperature overnight, then concentrated and the residue was partitioned between EtOAc/water. The aqueous layer was back extracted and combined organics were dried over MgSO4, filtered and concentrated to afford a brown oil. This material was purified via flash column chromatography, eluting with 2-50% EtOAc/Hept. Relevant fractions were pooled and concentrated to afford a clear oil—797 mg (97% yield).

1. additionwas added
2. concentrationconcentrated
3. customthe residue was partitioned between EtOAc/water
4. extractionThe aqueous layer was back extracted
5. dry with materialcombined organics were dried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated
8. customto afford a brown oil
9. customThis material was purified via flash column chromatography
10. washeluting with 2-50% EtOAc/Hept
11. concentrationconcentrated
12. customto afford a clear oil—797 mg (97% yield)