2-Thiophenecarboxylicacid,5-ethynyl-(9CI) synthesis
- Product Name:2-Thiophenecarboxylicacid,5-ethynyl-(9CI)
- CAS Number:174672-58-3
- Molecular formula:C7H4O2S
- Molecular Weight:152.17
![2-Thiophenecarboxylic acid, 5-[2-(trimethylsilyl)ethynyl]-, ethyl ester](/CAS/20210305/GIF/881736-66-9.gif)
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Yield:174672-58-3 80%
Reaction Conditions:
Stage #1: ethyl 5-(2-trimethylsilyl-ethyn-1-yl)-thiophene-2-carboxylatewith sodium hydroxide;water in ethanol at 50; for 4 h;
Stage #2: with hydrogenchloride in water;
Steps:
2.c
A solution of 9.93 g (39 mmol) of ethyl-5-(2-trimethylsilyl)ethynyl-thiophenecarboxylic acid (see WO1996/03407 for preparation) in 50 ml of ethanol is stirred with 200 ml of 2M NaOH at 50° C. for 4 h. The mixture is then concentrated in vac., mixed with water and extracted 2× with methylene chloride. The aqueous phase is acidified with HCl and cooled, and the precipitate which separates out is filtered off with suction. Yield: 4.8 g (80%) Rf: 0.24 (silica gel; methylene chloride:MeOH 95:5) C7H4O4S*2HCl (152.17) Mass spectrum: (M-H)-=151
References:
US2006/69082,2006,A1 Location in patent:Page/Page column 26
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