Ethyl Acetate → HCID 89524688, compound

Temperature

-78 °C

To a solution of Example 85E (1.45 g, 6.45 mmol) in DCM (50 mL) was added dropwise a solution of DIBAL (7.74 mL, 7.74 mmol, IM in toluene) at −78° C. under nitrogen. After stirring for 3 hours at −78° C., the reaction was quenched with saturated NH4Cl (10 mL) and the resulting mixture was extracted with dichloromethane (30 mLx2). The combined organic layers were washed with water (20 mL) and brine (20 mL), dried over Na2SO4, filtered, and concentrated. The residue was purified by column chromatography eluting with petroleum ether:EtOAc=100:1-100:3 to provide the title compound (733 mg, 3.2 mmol, 49% yield) as colorless oil. LC-MS: m/z 230 (M+H)+.

1. customthe reaction was quenched with saturated NH4Cl (10 mL)
2. extractionthe resulting mixture was extracted with dichloromethane (30 mLx2)
3. washThe combined organic layers were washed with water (20 mL) and brine (20 mL)
4. dry with materialdried over Na2SO4
5. filtrationfiltered
6. concentrationconcentrated
7. customThe residue was purified by column chromatography
8. washeluting with petroleum ether

ORD record

ord-f90047ad24b94526b2c72a18ef5de3d8

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08772500B2