Reaktion #673830

Reaktionsgleichung

3-iodo-but-2Z-en-1-ol

Na2CO3

Bis(pinacolato)diboron

potassium acetate

Intermediate 1

6-Bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene

→

title compound

Ausbeute 77.4%

3-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-but-2Z-en-1-ol

Ausbeute 77.4%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling to room temperature
2. 2
   workup.STIRRINGwas then stirred at 80° C. for another 24 h
3. 3
   SonstigeThe reaction was finally quenched with water (20 mL)
4. 4
   Extraktionextracted with ether (3×10 mL)
5. 5
   WaschenThe organic layer was washed with brine (2×10 mL)
6. 6
   Trocknendried (MgSO4)
7. 7
   Einengenconcentrated
8. 8
   Sonstigeto give a crude brown oil
9. 9
   SonstigeThe crude product was purified by flash chromatography

Vorschrift

Bis(pinacolato)diboron (5.8 g, 22.5 mmol), potassium acetate (4.5 g, 45 mmol) and [1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium (PdCl2(dppf)2) (500 mg, 0.6 mmol) were added to a solution of Intermediate 1 (4 g, 15 mmol) in 50 mL of DMF under argon. The mixture was then stirred at 80° C. for 24 h. After cooling to room temperature, 3-iodo-but-2Z-en-1-ol (6 g, 30 mmol), 2M Na2CO3 (30 ml), and PdCl2(dppf)2 (500 mg, 0.6 mmol) were added to the mixture, which was then stirred at 80° C. for another 24 h. The reaction was finally quenched with water (20 mL) and extracted with ether (3×10 mL). The organic layer was washed with brine (2×10 mL), dried (MgSO4) and concentrated to give a crude brown oil. The crude product was purified by flash chromatography using 20% EtOAc in hexane to give the title compound (3 g, 77% yield) as a colorless oil:

Quelle