Ethyl 3-phenylpropionate synthesis
- Product Name:Ethyl 3-phenylpropionate
- CAS Number:2021-28-5
- Molecular formula:C11H14O2
- Molecular Weight:178.23
64-17-5
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501-52-0
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2021-28-5
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Yield:2021-28-5 99%
Reaction Conditions:
with fluorosulfonyl fluoride;N-ethyl-N,N-diisopropylamine in 1,2-dichloro-ethane at 20; for 5 h;
Steps:
Esterification; General Procedure
General procedure: Carboxylic acid 1 (1.0 mmol, 1.0 equiv), alcohol 2 (2.0 mmol, 2.0 equiv), DIPEA (3.0 mmol, 3.0 equiv) and DCE (the reaction mixture was diluted to 0.2 M) were added to an oven-dried 25 mL reaction flask equipped with a stir bar and sealed with a rubber stopper. SO2F2 gas was introduced into the stirred reaction mixture by slowly bubbling from a balloon [the balloons were made from low-density polyethylene (LDPE) which it not reactive with SO2F2]. The reaction mixture was stirred at room temperature for 5 h. After the reaction was completed, the reaction mixture was directly concentrated under vacuum and was purified by column chromatography on silica gel using a mixture of petroleum ether and ethyl acetate as eluent to give the desired product 3. To confirm the amount of SO2F2 consumed in this transformation, 4-biphenylcarboxylic acid (1a) (10 mmol, 1.0 equiv), EtOH (2a) (20 mmol, 2.0 equiv), DIPEA (30 mmol, 3 equiv) and DCE (the reaction mixture was diluted to 0.2 M) were added to an oven-dried 100 mL reaction flask equipped with a stir bar and sealed with a rubber stopper. A balloon filled with SO2F2 gas was weighed before introduction of the SO2F2 gas into the stirring reaction mixture by slow bubbling at room temperature. After the reaction complete, the SO2F2 balloon was weighed again to measure the difference in weight. It was calculated that the SO2F2 consumption was about 3.26 g (31.9 mmol, 3.2 equiv) in this particular reaction (some of the gas dissolved in the DCE solvent can be considered as unreacted but consumed). The corresponding ester product 3a was obtained in 98% yield after work-up.
References:
Qin, Hua-Li;S Alharbi, Njud;Wang, Shi-Meng [Synthesis,2019,vol. 51,# 20,p. 3901 - 3907]
140-88-5
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98-80-6
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2021-28-5
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2216-94-6
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2021-28-5
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103-36-6
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2021-28-5
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4192-77-2
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2021-28-5
266 suppliers
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