Aluminium lithium hydride → HCID 12391212, compound

To a solution of methyl 3-(2,4-dichlorophenyl)-2-(4-chorophenyl)propionate (6.4 g, 8.6 mmol) in 50 mL ether at −40° C. was added lithium aluminum hydride (1.4 g, 37 mmol), and the reaction was allowed to warm to room temperature over 2 h. The reaction was quenched by addition of MeOH (3 mL) dropwise at −10° C., and the mixture was partitioned between 100 mL saturated ammonium chloride and EtOAc (100 mL). The organic layer was separated and the aqueous layer extracted with EtOAc (2×100 mL). The combined organic extracts were dried over anhydrous MgSO4, filtered, and concentrated to dryness to give the title compound, which was used without further purification. 1H NMR (400 MHz, CD3OD): δ 7.4-6.9 (m, 7H), 3.72 (m, 2H), 3.24 (dd, 1H), 3.16 (m, 1H), 2.85 (dd, 1H).

1. customThe reaction was quenched by addition of MeOH (3 mL) dropwise at −10° C.
2. customthe mixture was partitioned between 100 mL saturated ammonium chloride and EtOAc (100 mL)
3. customThe organic layer was separated
4. extractionthe aqueous layer extracted with EtOAc (2×100 mL)
5. dry with materialThe combined organic extracts were dried over anhydrous MgSO4
6. filtrationfiltered
7. concentrationconcentrated to dryness

ORD record

ord-4d84c77dac83419797837e63fd1c8f85

Source dataset

uspto-grants-2009_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07550489B2