Reaction Steps
To a solution of (S)-1,4-dibenzyloxy-2-(methoxymethoxy)butane (2 g, 6 mmol) in methanol (14 ml) was added a 2% solution of methanolic hydrogen chloride (6 ml, 2.5 mmol). The solution was stirred at room temperature for 7 hours, the solvent removed and the residue chromatographed on silica eluting with ethyl acetate hexane 1:1 to give (S)-1,4-dibenzyloxy-2-hydroxybutane (1.46 g, 84%), [α]D25 -7.3° (c 1.1 in ethanol); IR: υmax (film) 3450, 3080, 3060, 3015, 2920, 2860, 2800, 1950, 1870, 1810, 1605, 1585, 1495, 1450, 1365, 1310, 1260, 1205, 1100, 1030, 1000, 950, 915, 820, 805, 760, 700, 610 cm-1 ; 1H NMR: δH (CDCl3) 1.79 (2H, d, t J=6 Hz and 6 Hz, CH2), 2.86 (1H, d, J=3 Hz, D2O exchangeable, OH), 3.45 (2H, m, CH2), 3.65 (2H, m, CH2), 4.05 (1H, m, CH), 4.51 (2H, s, CH2), 4.55 (2H, s, CH2), 7.3 (10H, m, 2×C6H5). Found: C, 75.64; H, 7.87%. C18H22O3 requires: C, 75.50; H, 7.74%.
