تفاعل #2254207

معادلة التفاعل

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

المذيبات

CH2Cl2

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONThe resulting mix
2. 2
   أخرىThe reaction was quenched with H2O (10 ml)
3. 3
   workup.ADDITIONdiluted with CH2Cl2 (10 ml)
4. 4
   غسيلwashed with sat. NaHCO3 (20 ml), brine (20 ml)
5. 5
   أخرىdried
6. 6
   تركيزconcentrated
7. 7
   أخرىPurified by normal phase SiO2 chromatography (5 to 40% EtOAc/hexanes)

الإجراء التجريبي

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%).

المصدر