2'-Hydroxy-3-phenylpropiophenone synthesis
- Product Name:2'-Hydroxy-3-phenylpropiophenone
- CAS Number:3516-95-8
- Molecular formula:C15H14O2
- Molecular Weight:226.27
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Yield:-
Reaction Conditions:
Stage #1: 2-(trimethylsilyl)phenyl trifluoromethanesulfonate;3-Phenylpropionic acidwith sodium hydroxide in acetonitrile at 20; for 0.166667 h;Inert atmosphere;
Stage #2: with cesium fluoride in acetonitrile at 80; for 4 h;Inert atmosphere;Overall yield = 73 %; chemoselective reaction;
Steps:
Typical procedure for O-arylation of aliphatic carboxylic acids with arynes:
General procedure: Kobayashi silylaryl triflate 1 (0.68 mmol) and aliphatic carboxylic acid 2 (3.4 mmol) in acetonitrile(4.0 mL) was added sodium hydroxide (80 mg, 2.0 mmol) under nitrogen atmosphere. After stirringfor 10 minutes at room temperature, cesium fluoride (410 mg, 2.7 mmol) was then introduced. Themixture was stirred at 80 oC for 4 h. After removal of the solvent, the residue was then purified byflash column chromatography on silica gel (eluent = petroleum ether/ethyl acetate 10:1 v/v) to givethe desired product 3.
References:
Wen, Chunxiao;Chen, Qian;He, Zhenwen;Yan, Xinxing;Zhang, Changyuan;Du, Zhiyun;Zhang, Kun [Tetrahedron Letters,2015,vol. 56,# 40,p. 5470 - 5473] Location in patent:supporting information
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