Lithium tri-s-butylborohydride → HCID 178521629, compound

Participants

Reaction Conditions

Reaction Steps

In a 100 mL flask with 3-(benzyloxyethyl)cyclobutanone (2.5 g, 12.2 mmol) inside, dry THF 30 mL was added under argon to give a light yellow solution. This was cooled to −78° C., after a while, L-selectride (1.0 M in THF, 14.7 mL, 14.6 mmol) was added drop by drop and this was allowed to warm up to room temperature, after which the reaction was quenched with saturated NaHCO3. Then the mixture was cooled to 0° C. and 30% H2O2 was added drop by drop, followed by the addition of H2O and EtOAc. The organic phase was separated, washed with H2O twice and brine once, dried over MgSO4 and solvent evaporation gave the crude product, which was purified by silica gel flash chromatography (Hexane:EtOAc=3:1) to give a colorless oil (2.0 g, 79.4%, Rf=0.2 (Hexane:EtOAc=3:1)). 1H NMR (CDCl3, 300 MHz): δ 1.40-1.60 (m, 2H), 1.60-1.90 (m, 3H), 2.05-2.21 (bs, 1H), 2.38-2.50 (m, 2H), 3.32-3.44 (t, J=, 2H), 4.52 (s, 2H), 7.20-7.40 (m, 5H). 13C NMR (CDCl3, 75 MHz): δ 22.90, 37.08, 37.85, 39.91, 64.14, 68.78, 73.04, 127.62, 127.68, 128.45, 138.59. MS (FAB): expected for C13H18O2 (M+H)+ 207.28. Found 207.13801.

Provenance & Evidence