Aluminium lithium hydride → N-(4-formyl-5-phenyl-1,3-thiazol-2-yl)acetamide

Temperature

0 °C

Methyl 2-(acetylamino)-5-phenyl-1,3-thiazole-4-carboxylate (2.34 g) was suspended in THF (23 ml), and then lithium aluminium hydride (482 mg) was added portionwise to the solution at 0° C. The reaction mixture was stirred at 0° C. for 1.5 hours and quenched with MeOH. AcOEt and 1N HCl were added to the mixture, and the mixture was extracted. The aqueous layer was extracted with AcOEt (twice). The combined organic layer was washed with brine, dried over anhydrous MgSO4, and concentrated in vacuo. The residual solid was dissolved in MeOH (5 ml) and CHCl3 (90 ml). Then manganase(IV) oxide (11 g) was added to the solution under N2 atmosphere. The reaction mixture was stirred at r.t. for 13 hours, and filtered through a celite pad. The filtrate was concentrated in vacuo. The residue was purified by flash column chromatography over silica gel with CHCl3/MeOH (20:1) as an eluent to give N-(4-formyl-5-phenyl-1,3-thiazol-2-yl)acetamide (705.2 mg) as a brown amorphous substance.

1. customquenched with MeOH
2. additionAcOEt and 1N HCl were added to the mixture
3. extractionthe mixture was extracted
4. extractionThe aqueous layer was extracted with AcOEt (twice)
5. washThe combined organic layer was washed with brine
6. dry with materialdried over anhydrous MgSO4
7. concentrationconcentrated in vacuo
8. dissolutionThe residual solid was dissolved in MeOH (5 ml)
9. additionThen manganase(IV) oxide (11 g) was added to the solution under N2 atmosphere
10. stirringThe reaction mixture was stirred at r.t. for 13 hours
11. filtrationfiltered through a celite pad
12. concentrationThe filtrate was concentrated in vacuo
13. customThe residue was purified by flash column chromatography over silica gel with CHCl3/MeOH (20:1) as an eluent

ORD record

ord-2200abfc3cd24fb89bfb213dd2b1c8d8

Source dataset

uspto-grants-2008_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07442715B2