A Convenient Synthesis of 4-tert-Butyl-5-benzofuranols and Dihydrobenzofuranols

…, CG Caldwell, IE Kopka, ML Hammond

Index: Zambias, Robert A.; Caldwell, Charles G.; Kopka, Ihor E.; Hammond, Milton L. Journal of Organic Chemistry, 1988 , vol. 53, # 17 p. 4135 - 4137

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Citation Number: 13

Abstract

'Reagents:(a) CICHzCHO, NaOH, KI, HzO, 25" C, 58%;(b) t-BuLi, ether/hexane,-78 to 5" C, 47%;(c) BH3, THF, 4" C, then NaOH, H202, 50" C, 82%;(d)(COC1) 2, DMSO, Et3N,-78 to 25" C, 82%;(e) S8, 225" C, 2 h, 52%;(f) Hz, 40 psi, 10% Pd/C, HOAc, 25" C, 77%;(g) NaH, ethyl formate, toluene, 90 min, 25" C;(h) DDQ, benzene, 25" C, 45 min, 66%. drogenation (Scheme I). Addition of chloroacetaldehyde to 1, 3-cyclohexanedione by the method of ...