Aluminium lithium hydride → HCID 57753319, compound

To 23.6 mmol LiAlH4 in 10 ml THF was added dropwise over 5 min a solution of 3.93 mmol 4-fluoro-5-trifluoromethyl-phthalic acid dimethyl ester in 5 ml THF. The mixture was stirred at room temperature for 2 h, and then heated at 50° C. for 20 min. The reaction mixture was quenched by dropwise addition of 8 ml ethyl acetate, stirred for a further 15 min at 50° C., then cooled to room temperature and acidified to pH 1 by dropwise addition of 5 M aq HCl. The mixture was then partitioned between ethyl acetate and brine and the organic phase was then separated, dried over sodium sulfate, and concentrated in vacuo. The residue was purified by chromatography on silica gel (eluant: methanol/dichloromethane) to afford the title compound as a colourless oil (57% yield). MS (m/e): 283.1 ([M+OAc)]−, 100%), 223.1 ([M−H]−, 20%).

1. temperatureheated at 50° C. for 20 min
2. customThe reaction mixture was quenched by dropwise addition of 8 ml ethyl acetate
3. stirringstirred for a further 15 min at 50° C.
4. temperaturecooled to room temperature
5. additionacidified to pH 1 by dropwise addition of 5 M aq HCl
6. customThe mixture was then partitioned between ethyl acetate and brine
7. customthe organic phase was then separated
8. dry with materialdried over sodium sulfate
9. concentrationconcentrated in vacuo
10. customThe residue was purified by chromatography on silica gel (eluant: methanol/dichloromethane)

ORD record

ord-e3959a43527f425482495e86afa6df43

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08188139B2