Reaktion #1080642

Reaktionsgleichung

ethyl acetate

N-propionyl tyramine

sodium hydride

→

phenyl ether

Ausbeute 32.0%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGto stir at room temperature for 5 hours
2. 2
   Extraktionextracted with 10% sodium sulfate
3. 3
   TrocknenThe organic layer was dried over sodium sulfate
4. 4
   Sonstigeevaporated to dryness
5. 5
   Sonstigechromatographed on silica gel using a hexane-ethyl acetate gradient

Vorschrift

To a stirred solution of N-ethyl, N-propionyl tyramine (2.84 g, 12.83 mmole) in tetrahydrofuran (32.1 ml) was added 60% sodium hydride dispersion (0.56 g, 14.11 mmole). After stirring for 10 minutes, the compound of Example 42(E) (4.70 g, 12.83 mmole) was added. The reaction was allowed to stir at room temperature for 5 hours, poured into ethyl acetate, and extracted with 10% sodium sulfate, then brine. The organic layer was dried over sodium sulfate, evaporated to dryness, and chromatographed on silica gel using a hexane-ethyl acetate gradient. Further chromatography on silica gel using toluene-acetone gradients yielded the intermediate phenyl ether (2.10 g, 32%):

Quelle