Reaktion #2254207

Reaktionsgleichung

Allyltrimethylsilane

2,2-dimethyl-4-(4-methylphenyl)oxan-4-ol

BF3 OEt2

→

2,2-dimethyl-4-(4-methylphenyl)-4-(prop-2-en-1-yl)oxane

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONThe resulting mix
2. 2
   SonstigeThe reaction was quenched with H2O (10 ml)
3. 3
   workup.ADDITIONdiluted with CH2Cl2 (10 ml)
4. 4
   Waschenwashed with sat. NaHCO3 (20 ml), brine (20 ml)
5. 5
   Sonstigedried
6. 6
   Einengenconcentrated
7. 7
   SonstigePurified by normal phase SiO2 chromatography (5 to 40% EtOAc/hexanes)

Vorschrift

Allyltrimethylsilane (4.34 ml, 27.2 mmol) was added to a solution of 2,2-dimethyl-4-(4-methylphenyl)oxan-4-ol (3.0 g, 13.6 mmol) in dry CH2Cl2 (100 ml) at 0° C., followed by BF3—OEt2 (3.42 ml, 27.2 mmol). The resulting mix was stirred at 0° C. for 1 h. The reaction was quenched with H2O (10 ml) and diluted with CH2Cl2 (10 ml), and washed with sat. NaHCO3 (20 ml), brine (20 ml), dried and concentrated. Purified by normal phase SiO2 chromatography (5 to 40% EtOAc/hexanes) to give 2,2-dimethyl-4-(4-methylphenyl)-4-(prop-2-en-1-yl)oxane as a colorless oil, which was used crude (2.49 g, 75%).

Quelle