1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 56599324, compound

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Reaction Steps

6-Bromo-5-(4-chlorophenyl)-7-methylnaphthalen-2-ol (4.5 g, 12.9 mmol) was taken up in DCM (65 mL). Added to this solution were TIPSCl (4.1 mL, 19.4 mmol), DBU (3.5 mL, 23.2 mmol), and DMAP (0.16 g, 1.3 mmol). After stirring at room temperature overnight, the DCM was removed in vacuo and the residue taken up in hexane (200 mL). This solution was washed with 1 M HCl (100 mL) and the layers separated. Following extraction of the aqueous layer with hexanes, the combined organics were washed with brine, dried over anhydrous MgSO4 and concentrated in vacuo. The resulting residue was purified by Yamazen column chromatography (2-5% DCM/Hex) to afford 5.12 g (79%) of the title compound as a colorless syrup. 1H-NMR: 400 MHz, (CDCl3) δ: 7.61 (s, 1H); 7.49 (br d, J=8.4 Hz, 2H); 7.23 (br d, J=8.4 Hz, 2H); 7.17 (d, J=8.8 Hz, 1H), 7.16 (d, J=2.4 Hz, 1H); 6.95 (dd, J=8.8, 2.4 Hz; 1H); 2.60 (s, 3H); 1.30 (hep, J=7.2 Hz, 3H); 1.12 (d, J=7.2 Hz, 18H).

Provenance & Evidence