benzyl 3-(tetrahydro-2H-pyran-2-yloxy)propanoate → 1-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)cyclopropanol

Participants

Reaction Conditions

Reaction Steps

To a solution of benzyl 3-(tetrahydro-2H-pyran-2-yloxy)propanoate (1.1 g, 4.17 mmol) in 14.2 mL of THF was added Ti(Oi-Pr)4(0.252 mL, 0.834 mmol, 0.955 g/L, Aldrich) via a syringe under nitrogen at rt. The reaction mixture was then cooled to 18° C. over 30 min. EtMgBr (3.54 mL, 10.4 mmol, 3M ether solution, Aldrich) was added via a syringe pump over 2 hrs. The reaction was quenched with saturated NH4Cl solution (50 mL) when benzyl 3-(tetrahydro-2H-pyran-2-yloxy)propanoate reacted completely (monitored by TLC). The mixture was filtered and the filtrate was extracted with ethyl acetate (30 mL×3). The combined organic phases were dried over Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE: EtOAc=10:1) to give the desired compound as yellow oil (507 mg, 65%).

Provenance & Evidence