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) in 18 mL THF was added EtMgBr (4.5 mL, 13.25 mmol, Aldrich) dropwise over 2 hrs under N2. The reaction temperature was kept between 15 to 20° C. After stirring for 2 hrs, the reaction was quenched with 15 mL of saturated NH4Cl solution and extracted with EtOAc (20 mL×5). The combined organic phases were dried over Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE: EtOAc=5:1) to afford the title compound as colorless oil (500 mg, 55%).

1. customwas kept between 15 to 20° C
2. customthe reaction was quenched with 15 mL of saturated NH4Cl solution
3. extractionextracted with EtOAc (20 mL×5)
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 (PE: EtOAc=5:1)

ORD record

ord-0de37d2c6d13495a821bc88f8e1ab50b

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08232294B2