ethyl 2-((tetrahydro-2H-pyran-2-yl)oxy)acetate → 1-((tetrahydro-2H-pyran-2-yloxy)methyl)cyclopropanol

To a mixture of ethyl 2-(tetrahydro-2H-pyran-2-yloxy)acetate (1 g, 5.3 mmol) and Ti(O-iPr)4 (1.06 mL, 3.5 mmol, Aldrich) in 18 mL of THF under N2 was added EtMgBr (4.5 mL, 13.25 mmol, 3M ether solution, Aldrich) dropwise over 2 hrs, and the temperature must be kept at 15-20° C. After stirring for 2 hrs, and the reaction mixture was quenched with saturated NH4Cl aqueous solution at 0° C. and extracted with EtOAc (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 (20:1 (v/v) petroleum ether/EtOAc) to afford 1-((tetrahydro-2H-pyran-2-yloxy)methyl)cyclopropanol as colorless oil (500 mg, 55%).

1. custommust be kept at 15-20° C
2. customthe reaction mixture was quenched with saturated NH4Cl aqueous solution at 0° C.
3. extractionextracted with EtOAc (30 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 (20:1 (v/v) petroleum ether/EtOAc)

ORD record

ord-efeadf71670243409e13d1d76fbbaf3d

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08426585B2