Tetrahydrofuran → HCID 19902684, compound

Participants

Reaction Steps

To a solution of 4.0 g of 2,7-di-tert-butyl-9-trimethylsilyl-9-fluorenylmethyl benzyl ether in 20 mL of freshly distilled THF and 80 mL of 100% EtOH was added 0.8 g of 5% palladium on charcoal. The heterogeneous mixture was shaken under hydrogen at a pressure of 45 psi in a Parr apparatus for 2 hours. The catalyst was removed by filtration and rinsed with ether (2×10 mL). The filtrate was evaporated under reduced pressure to give 3.23 g (100%) of the crude alcohol as a yellow oil which was chromatographed on silica gel (230-400 mesh, 4×45-cm packed column) with an eluant consisting of Skelly B--ether (3:1), to give 3.12 g (96.4%) of the alcohol as a white solid. Recrystallization from Skelly B gave 2.57 g (79.44%) of the pure alcohol as white needles, m.p. 131°-132° C.; IR (KBr): 3545, 3495 cm-1 (OH); 1H NMR (CDCl3): δ -0.18 (s, 9H, SiMe3), 1.20 (b, 1H, OH), 1.39 (s, 18H, t-Bu), 4.50 (s, 2H, CH2), 7.20-7.90 (m, 6H, aryl).

Provenance & Evidence