Water → (R)-(+)-2-fluorooctanol

Participants

Reaction Steps

--Ethyl (R)-(+)-2-fluorooctanoate 69 (20.0 g, 105 mol) in dry THF (30 ml) was added dropwise with stirring to a suspension of lithium aluminium hydride (6 g, 0.158 mol) under nitrogen and with water bath cooling. After the final addition the water bath was removed and the mixture was stirred for 16 h. Aqueous THF (50 ml, 1:3) was added dropwise with iced water-bath cooling followed by 20% hydrochloric acid until a clear solution was effected. The mixture was extracted with ether (3 times) and the combined organic solutions were washed with sat. sodium bicarbonate solution (twice) and brine, dried (MgSO4) and evaporated. The yellow oil was distilled to give (R)-(+)-2-fluorooctanol 70 which solidified on cooling (12.9 g, 83%), b.p. 110° C. at 20 mm Hg, [α]D18 =+6.2° (c 4.6 in CHCl3); νmax /cm-1 (film) 3600-3100br (OH), 2920, 2860, 1460, 1375, 1125sh, 1055br and 840; δ 0.90 (3H, t, Me), 1.14-1.80 (10H, m), 2.19 (1H, br s, OH), 3.69 (2H, br d, 3JHF 27, CH2OH), and 4.56 (1H, br d, 2JHF 51, CHF); m/z 149 (M+ 1), 137, 125, 115, 111, 97, 81 and 69.

Provenance & Evidence