Reaction #985316

Reaction equation

1-(2-Hexylsulfanyl-6-methyl-pyrimidin-4-yl)-ethanol

Jones' reagent

H2SO4

→

white crystals

Yield 44.0%

1-(2-Hexylsulfanyl-6-methyl-pyrimidin-4-yl)-ethanone

Yield 44.0%

Solvents

acetone

Conditions

Workup

1. 1
   workup.ADDITIONwas add dropwise
2. 2
   Otherthe resulting green solution was decanted from the chromium salts
3. 3
   Extractionextracted with AcOEt and sat. NaCl solution
4. 4
   OtherThe crude product was purified by chromatography on silica gel with a heptane/AcOEt gradient

Procedure

1-(2-Hexylsulfanyl-6-methyl-pyrimidin-4-yl)-ethanol (2.2 g, 8.65 mmol) was dissolved under nitrogen in acetone (20 mL). Then 2 M Jones' reagent prepared from 20 g CrO3 in 100 mL 4 M H2SO4 (6.5 mL, 13 mmol) was add dropwise. After stirring for 2 h at 20° C., the resulting green solution was decanted from the chromium salts and extracted with AcOEt and sat. NaCl solution. The crude product was purified by chromatography on silica gel with a heptane/AcOEt gradient. One obtained 960 mg (44 %) of white crystals. MS: m/z=252 (M).

Source