Aluminium lithium hydride → HCID 21914903, compound

Participants

Reaction Steps

Ethyl 2-(acetylamino)-5-[3-(methylsulfonyl)benzyl]-1,3-thiazole-4-carboxylate (54.7 mg) was suspended in THF (1 ml) under N2 atmosphere, and then lithium aluminium hydride (7.79 mg) was added portionwise to the suspension at 0° C. The reaction mixture was refluxed for 2.5 hours, and quenched with MeOH and 1N—HCl at 0° C. Anhydrous MgSO4 was added to the mixture, and stirred at r.t. for 1 hour. The suspension was filtered in vacuo. The filtrate was concentrated in vacuo. The residual oil (114.8 mg), CHCl3 (1 ml), CH3CN (1 ml) and Dess-Martin periodinane (88 mg) were combined at 0° C. under N2 atmosphere. The reaction mixture was stirred at r.t. for 1 hour, and diluted in CHCl3. The organic solution was washed with saturated NaHCO3, water and brine, dried over anhydrous MgSO4, and concentrated in vacuo to give N-{4-formyl-5-[3-(methylsulfonyl)benzyl]-1,3-thiazol-2-yl}acetamide (61.2 mg) as a yellow amorphous.

Provenance & Evidence