Reaktion #316898

Reaktionsgleichung

2,6-Diformyl-4-bromophenol

1-dodecyne

→

title compound

Ausbeute 46.0%

2,6-Diformyl-4-(dodecyn-1-yl)phenol

Ausbeute 46.0%

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigedegassed benzene (1 mL)
2. 2
   SonstigeThe yellow suspension was sparged with argon for 30 min
3. 3
   Sonstigedegassed Et3N (1 mL)
4. 4
   workup.ADDITIONwas added
5. 5
   SonstigeThe resulting brown suspension was sealed in a pressure vial
6. 6
   SonstigeThe mixture was then partitioned between EtOAc and KHSO4 solution
7. 7
   SonstigeThe organic layer was separated
8. 8
   Waschenwashed with brine, dried MgSO4) and
9. 9
   Einengenconcentrated under reduced pressure
10. 10
    SonstigeThe dark yellow oil was purified by column chromatography on silica gel (25% Et2O in hexanes)

Vorschrift

2,6-Diformyl-4-bromophenol (2.50 g, 10.9 mmol), 1-dodecyne (2.00 g, 12.0 mmol), Cul (65 mg, 0.33 mmol), and bis(triphenylphosphine)palladium)II)dichloride were suspended in degassed acetonitrile (MeCN) (5 mL) and degassed benzene (1 mL). The yellow suspension was sparged with argon for 30 min and degassed Et3N (1 mL) was added. The resulting brown suspension was sealed in a pressure vial, warmed to 80° C. and held there for 12 h. The mixture was then partitioned between EtOAc and KHSO4 solution. The organic layer was separated, washed with brine, dried MgSO4) and concentrated under reduced pressure. The dark yellow oil was purified by column chromatography on silica gel (25% Et2O in hexanes) to give 1.56 g (46%) of the title compound.

Quelle