Tetrabutylammonium Fluoride → HCID 66960230, compound

Participants

Reaction Steps

A solution of TBS protected ether 50 (232 mg) in THF (10 mL) was treated with TBAF (0.5 mL, 1M solution in THF). After stirring overnight a standard aqueous work-up was carried out and the desired phenol 51 was purified by column chromatography (4:1 Hex/EA) to give a white solid which showed δH (400 MHz, CDCl3, ref. TMS=0) 6.77 (1H, s, ArH), 6.63 (1H, s, ArH), 5.50 (1H, s, OH), 3.85 (3H, s, ArOMe), 3.41-3.72 (5H, m, 2×OCH2 and CHOR), 3.40 (3H, s, OMe), 2.69-2.83 (6-CH2), 1.16-2.26 (13H, m) and 0.81 (3H, s, 18-Me); δC 144.5, 143.4, 131.7, 129.5 (all C), 114.6, 108.1, 89.6 (all CH), 72.3, 69.5 (both CH2), 59.1 (CH), 56.0 (CH3), 50.3, 44.2 (both CH), 43.3 (C), 38.6 (CH), 38.1, 28.9, 28.1, 27.2, 26.7, 23.0 (all CH2) and 11.6 (CH3).

Provenance & Evidence