Hydrogen Peroxide → 4-Benzyloxy-5-(4-fluorophenoxy)-1-pentanol

Participants

Reaction Conditions

Reaction Steps

A solution of boron trifluoroide.etherate (2.1 ml., 16.7 millimole) in dry tetrahydrofuran (15 ml.) is added dropwise to a stirred mixture of 4-benzyloxy-5-(4-fluorophenoxy)-1-pentene (2.86 g., 10 millimole) and sodium borohydride (0.47 g., 12.5 millimole) in dry tetrahydrofuran (25 ml.) maintained at 0°-5° C. under a nitrogen atmosphere. The resulting reaction mixture is warmed to 25° C. and maintained at 25° C. for 15 hours. After cooling to 0°-5° C., the reaction mixture is treated cautiously via successive dropwise additions of water (2 ml.), 5 N sodium hydroxide (4 ml.) and 30% hydrogen peroxide (8 ml.). After stirring at 25° C. for 1/2 hour, the resulting mixture is diluted with ice water and extracted with chloroform three times. The combined organic extract is washed with saturated aqueous brine, dried over magnesium sulfate, and filtered. Evaporation of the filtrate in vacuo provides the title compound as a viscous oil (3.0 g., 100%); pmr (CCl4) δ1.4-1.9 (4 H, m), 3.2-4.2 (6H, m), 4.58 (2H, broad s), 6.6-7.1 (4H, m) and 7.20 (5H, s).

Provenance & Evidence