Hydrochloric Acid → HCID 58877658, compound

Participants

Reaction Steps

Compound 5 (39.80 g, 96.5 mmol) was dissolved in EtOH (300 mL) and THF (300 mL). 1 M aqueous NaOH (250 mL, 250 mmol) was added and the solution refluxed for 2 h. The reaction was cooled to RT and then acidified to pH 2 with 6N aq. HCl. H2O (750 mL) and CH2Cl2 (500 mL) were added and the two layers were separated. The aqueous layer was extracted with CH2Cl2 (2×100 mL). The combined organics were dried (Na2SO4) and concentrated to provide the title compound, 6 (39.34 g, 100%), as a pale yellow solid. 1H NMR (400 MHz, DMSO-d6): δ 0.95 (t, J=7.4 Hz, 3H), 2.48 (q, J=7.4 Hz, 2H), 3.69 (s, 3H), 6.46 (d, J=15.8 Hz, 1H), 6.56 (d, J=8.6 Hz, 2H), 6.77 (d, J=8.6 Hz, 2H), 7.10-7.12 (m, 3H), 7.13-7.19 (m, 2H), 7.28 (d, J=8.3 Hz, 2H), 7.54 (d, J=8.3 Hz, 2H), 7.80 (d, J=15.8 Hz, 1H).

Provenance & Evidence