2-(prop-2-yn-1-yl)pent-4-ynoic acid synthesis
- Product Name:2-(prop-2-yn-1-yl)pent-4-ynoic acid
- CAS Number:65994-70-9
- Molecular formula:C8H8O2
- Molecular Weight:136.15
181478-00-2
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65994-70-9
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Yield:65994-70-9 95%
Reaction Conditions:
with sodium hydroxide in ethanol at 20; for 64 h;Reflux;
Steps:
6 Example 6: 2-(prop-2-yn-1-yl)pent-4-ynoic acid
[416] Example 6: 2-(prop-2-yn-1-yl)pent-4-ynoic acid 2M NaOH (2.6 mL, 5.2 mmol) was added to methyl 2-(prop-2-yn-1-yl)pent-4- ynoate (Org. Lett. 2008, 10(17), 3903) (383 mg, 2.55 mmol) before EtOH (19 mL) was added and the resulting solution heated to reflux for 22 h. The mixture was allowed to cool to rt and stirred for a further 42 h before the EtOH was removed under reduced pressure. The crude mixture was then diluted (Et20 and H20) and the Et20 fraction was extracted with H20 before discarding. The aqueous fractions were combined and acidified with 2M HCI to pH~1 before the product was extracted with Et20. The organic fractions were dried ( a2SC>4), filtered and concentrated under reduced pressure to provide the title compound (330 mg, 2.42 mmol, 95%) as a colourless solid which was used without further purification. 1H N R (400 MHz CDCI3): δ 2.83 (m, 1 H), 2.68 (m, 4H), 2.05 (t, J = 2.6 Hz, 2H). 13C NMR (100 MHz): δ 177.7, 80.2, 71.0, 42.9, 19.8.
References:
WO2014/134689,2014,A1 Location in patent:Paragraph 416
4431-32-7
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63104-44-9
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2689-88-5
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17920-23-9
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