Reacción #2254207

Ecuación de reacción

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

Disolventes

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONThe resulting mix
2. 2
   OtroThe reaction was quenched with H2O (10 ml)
3. 3
   workup.ADDITIONdiluted with CH2Cl2 (10 ml)
4. 4
   Lavadowashed with sat. NaHCO3 (20 ml), brine (20 ml)
5. 5
   Otrodried
6. 6
   Concentraciónconcentrated
7. 7
   OtroPurified by normal phase SiO2 chromatography (5 to 40% EtOAc/hexanes)

Procedimiento

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%).

Fuente