3,5-Dimethylisoxazole → HCID 57732079, compound

To a solution of 3,5-dimethylisoxazole (104 g, 1.07 mol, 1 eq) in THF (1 L) cooled to −78° C. under nitrogen, a solution of lithiumdiisopropylamide (1.8M ethylbenzene in THF) (630 mL, 1.134 mol, 1.06 eq) was added dropwise. After 1 hr, a solution of 3-chlorobenzaldehyde 100 g, 0.711 mole, 0.66 eq) in THF (300 mL) was added drop wise at −78° C. The reaction mixture was allowed to warm to room temperature and stirred overnight. It was cooled to 0° C., and quenched by saturated ammonium chloride solution (130 mL). The organic layer was concentrated to dryness. Water (1 L) was added to the residue was extracted with ethyl acetate (2×1 L). Combined organic extracts were washed with brine (700 mL) dried over anhydrous sodium sulfate. Concentrated and purified by column chromatography (50% ethyl acetate in hexane) over silica gel using a mixture of ethyl acetate and hexanes as eluant. The title compound was obtained as viscous brown oil (120 g, 0.507 mol, 48%).

1. temperatureIt was cooled to 0° C.
2. customquenched by saturated ammonium chloride solution (130 mL)
3. concentrationThe organic layer was concentrated to dryness
4. additionWater (1 L) was added to the residue
5. extractionwas extracted with ethyl acetate (2×1 L)
6. washCombined organic extracts were washed with brine (700 mL)
7. dry with materialdried over anhydrous sodium sulfate
8. concentrationConcentrated
9. custompurified by column chromatography (50% ethyl acetate in hexane) over silica gel using
10. additiona mixture of ethyl acetate and hexanes as eluant

ORD record

ord-7d1989c3d16245958bfcb831275ea7f9

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08357711B2