Reacción #565475

Ecuación de reacción

product

Methyl[(1,1-dimethyl-2-propynyl)oxy]acetate

sulfuric acid

→

title compound

Methyl (1,1-dimethyl-2-oxopropoxy)acetate

Disolventes

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaAfter refluxing for 1.5 hours
2. 2
   Concentraciónconcentrated to a volume of 100 mL
3. 3
   workup.ADDITIONpoured into 1N HCl (300 mL)
4. 4
   Extracciónextracted with dichloromethane (3×300 mL)
5. 5
   Lavadowashed with aqueous NaHCO3
6. 6
   Lavadowashed with brine
7. 7
   Secadodried over Na2SO4
8. 8
   Concentraciónconcentrated

Procedimiento

The product from Example 66A (10.0 g, 64 mmol) in methanol (320 mL) was treated with mercury(II) acetate (2.0 g, 6.4 mmol) and sulfuric acid (0.5 mL). After refluxing for 1.5 hours, the mixture was allowed to cool to ambient temperature, concentrated to a volume of 100 mL, poured into 1N HCl (300 mL) and extracted with dichloromethane (3×300 mL). The organic layers were combined, washed with aqueous NaHCO3, washed with brine, dried over Na2SO4 and concentrated to provide the title compound (10.3 g).

Fuente