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

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): 82.65 (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).

1. stirringstirring
2. waitcontinued for 20 min. at −78° C
3. stirringafter stirring for 1 h at −78° C.
4. customthe reaction was quenched
5. additionby adding aqueous NH4Cl
6. extractionThe organic materials were extracted with ethyl acetate
7. dry with materialdried (Na2SO4)
8. concentrationconcentrated under vacuum
9. customThe crude product was purified on a silica gel column

ORDレコード

ord-05cce9dd9dc1402b8ad62c16aa766e9e

出典データセット

uspto-grants-2001_10

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06306895B1