Methyl acetoacetate → Methyl 2-acetylpentanoate

Temperature

0 °C

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

1. stirringThe mixture is then stirred
2. temperatureat reflux for 6 hours
3. customThe solvent is removed in vacuo and water (200 mL) and EtOAc (200 mL)
4. additionare added
5. customThe layers are separated
6. extractionthe aqueous layer is extracted with EtOAc (200 mL)
7. washThe combined extracts are washed with brine (200 mL)
8. dry with materialdried (Na2SO4)
9. customEvaporation of the solvent
10. customprovides a light yellow oil
11. washFlash column chromatography of the residue by silica gel, eluting with 7:1 hexane, EtOAc

ORD record

ord-38e412d5df0d4503843df07d72e7b457

Source dataset

uspto-grants-2005_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06951864B2