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

Temperature

18 °C

To a mixture of benzyl 3-(tetrahydro-2H-pyran-2-yloxy)propanoate (4.2 g, 15.9 mmol) in 60 mL of THF was added Ti(Oi-Pr)4 (2.4 mL, 07.95 mmol, d=0.955 g/L, Aldrich) via a syringe under nitrogen at rt. After stirring at 18° C. for 30 min, EtMgBr (13.25 mL, 3.975 mmol, 3M ether solution, Aldrich) was added via a syringe pump over 3 hrs. The reaction was quenched with 50 mL of water. The mixture was filtered through a celite pad and the filtrate was extracted with ethyl acetate (100 mL×3). The combined organic phases were dried over Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (10:1 (v/v) petroleum ether/EtOAc) to afford the title compound as colorless oil (2.56 g, 86.5%).

1. customThe reaction was quenched with 50 mL of water
2. filtrationThe mixture was filtered through a celite pad
3. extractionthe filtrate was extracted with ethyl acetate (100 mL×3)
4. dry with materialThe combined organic phases were dried over Na2SO4
5. concentrationconcentrated in vacuo
6. customThe residue was purified by a silica gel column chromatography (10:1 (v/v) petroleum ether/EtOAc)

ORD record

ord-fcc08e5d6c92480b9e40129e6924d8db

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08232294B2