Hydrochloric Acid → HCID 25010499, compound

Participants

Reaction Steps

Ethyl-(2E,4E,8Z,11Z,14Z,17Z)-2-ethyl-eicosa-2,4,8,11,14,17-hexaneoate (17) (0.040 g, 0.112 mmol) was dissolved in ethanol (4 mL) and added a solution of LiOH×H2O (0.038 g, 0.898 mmol) in water (1 mL). The mixture was stirred at ambient temperature for 15 hours, followed by five hours at 70° C. The mixture was cooled, added 1M HCl until pH=1 and diluted with water (2 mL). The mixture was extracted twice with heptane (10 mL) and the combined organic extracts were dried (Na2SO4). Purification by flash chromatography (heptane:EtOAc 95:5 then 4:1) afforded 0.028 g (76%) of the title compound as a pale yellow oil. 1H-NMR (200 MHz, CDCl3): δ 0.90-1.07 (2×t, 6H), 2.00-2.10 (m, 2H), 2.20-2.30 (m, 4H), 2.35-2.50 (q, 2H), 2.75-2.90 (m, 6H), 5.27-5.44 (m, 8H), 6.05-6.20 (m, 1H), 6.30-6.43 (m, 1H), 7.50-7.70 (m, 1H); MS (electrospray): 327.2 [M−H]−.

Provenance & Evidence