反応 #2254207

反応方程式

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

溶媒

CH2Cl2

反応条件

後処理

1. 1
   workup.ADDITIONThe resulting mix
2. 2
   その他The reaction was quenched with H2O (10 ml)
3. 3
   workup.ADDITIONdiluted with CH2Cl2 (10 ml)
4. 4
   洗浄washed with sat. NaHCO3 (20 ml), brine (20 ml)
5. 5
   その他dried
6. 6
   濃縮concentrated
7. 7
   その他Purified by normal phase SiO2 chromatography (5 to 40% EtOAc/hexanes)

実験手順

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%).

出典