HCID 67296888, compound → HCID 67296782, compound

To a solution of 4-(tetrahydro-2H-pyran-2-yloxy)-dihydrofuran-2(3H)-one (2.23 g, 12 mmol) and Ti(Oi-Pr)4 (0.68 g, 2.4 mmol, Aldrich) in 40 mL of dry THF at 15° C. under N2 was added EtMgBr (30 mmol, 10 mL, 3M ether solution, Aldrich) dropwise via a syringe pump over 2 hrs. The temperature of the reaction was always kept below 20° C. After stirring for 2 hrs, the reaction mixture was quenched with 30 mL of saturated NH4Cl aqueous solution, and was extracted with ethyl acetate (50 mL×3). The combined organic phases were dried over Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (1:1 (v/v) EtOAc/n-hexane) to afford 1-(3-hydroxy-2-(tetrahydro-2H-pyran-2-yloxy)propyl)cyclopropanol as yellow oil (1.92 g, 73%).2

1. customwas always kept below 20° C
2. customthe reaction mixture was quenched with 30 mL of saturated NH4Cl aqueous solution
3. extractionwas extracted with ethyl acetate (50 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 (1:1 (v/v) EtOAc/n-hexane)

ORD record

ord-51cfe7c3757c4bb08402b43c8f4c0e72

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08426585B2