Potassium Carbonate → HCID 19595645, compound

Participants

Reaction Steps

To a solution of the above indane 14 (0.36 g, 1.37 mmol) dissolved in 15 rnd. MeOH was added solid K2CO3 (0.38 g, 2.74 mmol). The reaction mixture was allowed to stir overnight at room temperature. MeOH was evaporated and the residue was diluted with 10 mL of water. The aqueous layer was then acidified with 5% HCl until pH=4 or 5. Aqueous layer was extracted with EtOAc (2×10 mL). Then the organic layer was washed with saturated NaCl and dried with Na2SO4. Organics were concentrated in vacuo to provide 0.25 g of the 6-t-butyl-1,1-dimethyl-indan-4-ol intermediate in 84% yield that was used directly into the next step. A solution of the above indane (0.25 g, 1.15 mmol) dissolved in 2 mL of dry pyridine was cooled to 0° C. Trifluoroacetic anhydride (0.36 mL, 2.13 mmol) was slowly added. Resulting mixture was allowed to warm to room temperature and was allowed to stir overnight. Reaction mixture was poured into 15 mL of water and extracted with ether (2×10 mL). Ether extract was sequentially washed with water (10 mL), 10% aq. HCl (2×10 mL), water (10 mL), and saturated NaCl. Organics were then dried with Na2SO4 and concentrated in vacuo to give 6-t-butyl-1,1-dimethyl-indan-4-ol triflate (15) as a clear oil in 77% yield. 1H NMR (400 MHz, CDCl3) δ7.13 (d, J=1.4 Hz, 1H, aromatic), 7.01 (d, J=1.2 Hz, 1H, aromatic), 2.95 (t, J=7.2 Hz, 2H, aliphatic CH2), 1.97 (t, J=7.2 Hz, 2H, aliphatic CH2), 1.31 (s, 9H, aliphatic 3CH3) 1.27 (s, 6H, aliphatic 2CH3).

Provenance & Evidence