Method for synthesizing 3-aryl allyl group ether
A kind of technology of aryl allyl ether and synthesis method, which is applied in ether preparation, organic chemistry, etc., can solve the problems of non-recyclable metal, harm to human body and environment, instability of allyl tin, etc., and achieve moderate activity and low price Inexpensive, easy to operate and convenient effect
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Embodiment 1
[0017] Ferric chloride catalyzes the reaction of benzaldehyde with allyltriethoxysilane to prepare 3-phenylallyl ethyl ether.
[0018] Put a 10ml glass bottle with a rubber stopper on the 85-2 type constant temperature magnetic stirrer, add 2ml of nitromethane, 0.106g (1mmol) benzaldehyde, 0.224g (1.1mmol) allyltriethoxysilane, quickly Weigh 0.0162g (0.1mmol) of ferric trichloride into the reaction bottle, and cover with a rubber stopper. Then stir at room temperature for 3 hours to react. Then extracted three times with 1:1 petroleum ether / diethyl ether (15ml×3), combined the organic phases, dried over anhydrous sodium sulfate, and evaporated the solvent under reduced pressure to obtain 1.67g of oily liquid product with a yield of 95%. m / z176(M + )135(100)107(79)79(63) 1 H NMR (400MHz, CDCl 3 ) 7.30 (m 5H) 5.77 (m 1H) 5.34 (m 2H) 4.26 (t J = 8.0Hz 1H) 3.36 (m 2H) 2.57 (m 1H) 2.40 (m 1H) 1.18 (t J = 8.0Hz 3H) 13 C NMR (100MHz, CDCl 3 ) 142.26 134.84 128.12 127.28 126.48 ...
Embodiment 2
[0020] Ferric chloride catalyzes the reaction of o-chlorobenzaldehyde and allyl triethoxysilane to prepare 3-(1-chlorophenyl) allyl ethyl ether.
[0021] Put a 10ml glass bottle with a rubber stopper on the 85-2 type constant temperature magnetic stirrer, add 2ml of nitromethane, 0.141g (1mmol) o-chlorobenzaldehyde, 0.224g (1.1mmol) allyltriethoxysilane , quickly weighed 0.0162g (0.1mmol) ferric chloride into the reaction bottle, and covered with a rubber stopper. Then it was stirred for 3 hours at normal temperature. Then it was extracted three times with 1:1 petroleum ether / diethyl ether (15mlx3), the organic phases were combined, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 0.202 g of an oily liquid product with a yield of 96%. m / z210(M + )171(28)169(84)141(100)113(30) 1 H NMR (400MHz, CDCl 3 )7.49(m 1H)7.30(m 2H)7.20(m 1H)5.87(m 1H)5.05(m 2H)3.87(m 1H)3.38(m 2H)2.46(m 2H)1.19(t J=8.0Hz 3H) 13 C NMR (100MHz, CDCl ...
Embodiment 3
[0023] Indium trichloride catalyzes the reaction of p-bromobenzaldehyde with allyl triethoxysilane to prepare 3-(3-bromophenyl) allyl ethyl ether.
[0024] Put a 10ml glass bottle with a rubber stopper on the 85-2 type constant temperature magnetic stirrer, add 2ml of dichloromethane, 0.185g (1mmol) p-bromobenzaldehyde, 0.224g (1.1mmol) allyltriethoxysilane , quickly weighed 0.0221g (0.1mmol) indium trichloride, 0.163g (1.5mmol) trimethylchlorosilane and added to the bottle. Then it was stirred for 3 hours at normal temperature. Then extracted three times with 1:1 petroleum ether / diethyl ether (15mlx3), combined the organic phases, dried over anhydrous sodium sulfate, and evaporated the solvent under reduced pressure to obtain 0.225g of oily liquid product with a yield of 96%. m / z255(M + )215(92)213(100)187(75)185(89)157(32)77(62) 1 H NMR (400MHz, CDCl 3 ) 7.46 (d J = 8.0Hz 2H) 7.18 (d J = 8.0Hz 2H) 5.74 (m 1H) 5.02 (m 2H) 4.23 (t J = 6.0Hz 1H) 3.34 (m 2H) 2.54 (m 1H) 2.35...
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