Reaction #985315

Reaction equation

5-Hydroxy-hex-3-yn-2-one

2-hexyl-isothiourea hydrobromide

triethylamine

→

light yellow oil

Yield 61.1%

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

Yield 61.1%

Solvents

THF

Conditions

Workup

1. 1
   ExtractionThe mixture was extracted with AcOEt and sat. NH4Cl solution
2. 2
   OtherThe crude product was purified by chromatography on silica gel with a heptane/AcOEt gradient

Procedure

5-Hydroxy-hex-3-yn-2-one (2 g, 18 mmol) and 2-hexyl-isothiourea hydrobromide (5.2 g, 21 mmol) were dissolved in THF (10 mL). Then the triethylamine (5.5 mL, 40 mmol) was added and stirring continued for 3 h. The reaction was slightly exothermic. The mixture was extracted with AcOEt and sat. NH4Cl solution. The crude product was purified by chromatography on silica gel with a heptane/AcOEt gradient. One obtained 2.8 g (61%) of a light yellow oil. MS: m/z=254 (M)

Source