ChemicalBook CAS DataBase List 2-(prop-2-yn-1-yl)pent-4-ynoic acid

2-(prop-2-yn-1-yl)pent-4-ynoic acid synthesis

8synthesis methods

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