Réaction #53385

Équation de réaction

3-butyn-1-ol

1-Bromo-2,4-dimethoxybenzene

triphenylphosphine

→

Compound 75

Rendement 44.3%

4-(2,4-Dimethoxyphenyl)-but-3-yn-1-ol

Rendement 44.3%

Solvants

diethylamine

Conditions de réaction

Traitement

1. 1
   FiltrationThe catalyst was filtered off from the reaction mixture
2. 2
   workup.ADDITIONthe same amount of palladium chloride, triphenylphosphine, copper (I) iodide and 3-butyn-1-ol were added
3. 3
   workup.STIRRINGThe reaction mixture was stirred
4. 4
   Températureheated at 85° C. for 48 hours
5. 5
   AutreThen the solvent was removed at reduced pressure and water (approx. 100 mL)
6. 6
   workup.ADDITIONwas added to the residue
7. 7
   ExtractionThe mixture was extracted with ethyl acetate (350 mL)
8. 8
   Concentrationconcentrated
9. 9
   AutreThe product was purified by flash chromatography (silica gel, 1:1 hexanes/ethyl acetate)

Mode opératoire

1-Bromo-2,4-dimethoxybenzene (10 g 0.046 mol), palladium chloride (0.2 g 0.11 mmol) and triphenylphosphine (0.6 g 0.0023 mol) were dissolved in diethylamine (100 mL) under a nitrogen atmosphere. Copper (I) iodide (0.44 g 0.0023 mol) and 3-butyn-1-ol (7 mL 0.092 mol) were added into the reaction mixture at once. The mixture was stirred overnight at 55° C. under a nitrogen atmosphere. The catalyst was filtered off from the reaction mixture and the same amount of palladium chloride, triphenylphosphine, copper (I) iodide and 3-butyn-1-ol were added. The reaction mixture was stirred and heated at 85° C. for 48 hours. Then the solvent was removed at reduced pressure and water (approx. 100 mL) was added to the residue. The mixture was extracted with ethyl acetate (350 mL) passed through a pad of silica gel and concentrated. The product was purified by flash chromatography (silica gel, 1:1 hexanes/ethyl acetate). Compound 75 (4.2 g, 24%) was isolated as a brown oil. 1H NMR (300 MHz, CDCl3) δ2.24 (t, 1H), 2.73 (t, 2H), 3.80 (br s, 5H), 3.87 (s, 3H), 6.43 (m, 2H), 7.30 (m, 1H).

Source