Methyl acetoacetate → Methyl 2-acetylpentanoate

Participants

Reaction Conditions

Reaction Steps

A solution of methyl acetoacetate (10.8 mL, 100 mmol) in DME (50 mL) is added dropwise to a suspension of NaH (95% dry, 2.44 g, 100 mmol) in DME (250 mL) cooled to 0° C. The resulting solution is stirred at room temperature for 1 hour. Bu4NI (3.7 g, 10 mmol) is added, followed by PrI. The mixture is then stirred at reflux for 6 hours. The solvent is removed in vacuo and water (200 mL) and EtOAc (200 mL) are added. The layers are separated and the aqueous layer is extracted with EtOAc (200 mL). The combined extracts are washed with brine (200 mL) and dried (Na2SO4). Evaporation of the solvent provides a light yellow oil. Flash column chromatography of the residue by silica gel, eluting with 7:1 hexane, EtOAc provides the title product as a colorless oil. LC-MS, M+1 159.2 2. Preparation of 6-methyl-5-propyl-2-thio-2,3-dihydropyrimidin-4-one

Provenance & Evidence