Boron trifluoride etherate → (2s)-6-Benzyloxy-1-(4-fluorophenoxy)-hex-4-yn-2-ol

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Reaction Steps

To a solution of benzyloxy prop-2-yne (2.3 g, 16 mmol) in dry THF (25 ml ) at −78° C. was added n-BuLi in hexane (10.7 ml 16 mmol) and the mixture stirred for 20 min. Borontrifluoride etherate (2 ml , 16 mmol) was then added to the solution and stirring continued for 20 min. at −78° C. A THF solution of (S)-glycidol-4-fluorophenyl ether (1.8 g, 10.7 mmol) was added and after stirring for 1 h at −78° C., the reaction was quenched by adding aqueous NH4Cl. The organic materials were extracted with ethyl acetate, dried (Na2SO4) and concentrated under vacuum. The crude product was purified on a silica gel column using EtOAc-light petroleum (1:4) as eluent to give (2S)-6-benzyloxy-1-(4-fluorophenoxy)-hex-4-yn-2-ol (2 g, 65%) as a yellow colour liquid. TLC:ethyl acetate-light petroleum (1:3), Rf=0.4. 1H NMR (CDCl3, 200 MHz): δ 2.65 (m, 2H), 3.95-4.10 (m, 2H), 4.13-4.21 (m, 3H), 4.6 (s, 2H), 6.8-7.02 (m, 4H), 7.30-7.38 (m, 5H).

Provenance & Evidence