Reaktion #43626

Reaktionsgleichung

water

2-chloro-4-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-6-(methyloxy)pyridine

Cy2NMe

n-butyl acrylate

→

desired product

Ausbeute 68.0%

Butyl (2E)-3-[4-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-6-(methyloxy)-2-pyridinyl]-2-propenoate

Ausbeute 68.0%

Lösungsmittel

1,4-dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted 3× with diethyl ether
2. 2
   Trocknendried (magnesium sulphate)
3. 3
   Sonstigeevaporated
4. 4
   Sonstigechromatographed on silica gel (250 g)
5. 5
   Wascheneluting with 1:4 ethyl acetate-hexane

Vorschrift

A solution of 2-chloro-4-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-6-(methyloxy)pyridine (9.20 g, 32.01 mmol) in 1,4-dioxane (100 ml) was treated with Pd(Pt-Bu3)2 (327 mg, 0.64 mmol), Pd2(dba)3 (293 mg, 0.32 mmol), Cy2NMe (7.53 ml, 35.21 mmol) and n-butyl acrylate (5.96 ml, 41.62 mmol). The reaction was heated at 120° C. for 1 h and was then treated with water extracted 3× with diethyl ether, dried (magnesium sulphate), evaporated and chromatographed on silica gel (250 g), eluting with 1:4 ethyl acetate-hexane to give the desired product (8.25 g, 68%).

Quelle