2',4'-Dihydroxyacetophenone → HCID 12016857, compound

Participants

Reaction Steps

A solution of 20% lithiumhexamethyldisilazane in tetrahydrofuran (200.8 mL, 240 mmol), 2,4-dihydroxy acetophenone, 14 (9.12 g, 60 mmol) in tetrahydrofuran (150 mL) and ethyl-3,4-dibenzyloxy benzoate, 9 (21.7 g, 60 mmol) in tetrahydrofuran (100 mL) were reacted to afford 17, 1-(3,4-bis-benzyloxy-phenyl)-3-(2,4-dihydroxy-phenyl)-propane-1,3-dione (55 g), which was then cyclized with Dowex-H+ (12 g) in 2-propanol (400 mL) in a similar way as described for 22 to afford 23 (Frederique, A. A. A.; Hageman, J. A.; Guido, R. M. M. H.; Van Der Vijgh, W. J. F.; Bast, A.; Menge, W. M. P. B. J. Med. Chem. 2000, 43, 3752.). Yield 24 g (89%); mp 245-247° C. (lit. 244-245° C.); MS (FAB) 451 (M++1); IR (KBr) 3426, 1607; 1H NMR (200 MHz, DMSO-d6) δ 10.79 (s, 1H), 7.86 (d, J=8.6 Hz, 1H), 7.68 (s, 1H), 7.60 (d, J=8.8 Hz, 1H), 7.51-7.30 (m, 10H), 7.18 (d, J=8.5 Hz, 1H), 6.98 (s, 1H), 6.91 (d, J=8.8 Hz, 1H), 6.83 (s, 1H), 5.26 (s, 2H), 5.21 (s, 2H).

Provenance & Evidence