Malonic Acid → HCID 86644213, compound

At room temp., a piperidinium acetate solution, freshly prepared by mixing piperidine (110 μL, 1.10 mmol) and acetic acid (65.0 μL, 1.10 mmol) in dimethyl sulfoxide (5.00 mL), was injected into a stirred solution of the prepared oct-6-ynal (6.70 g, 54.0 mmol) and malonic acid (11.2 g, 108 mmol) in dimethyl sulfoxide (200 mL). After refluxing the reaction mixture for 4 h, water (50 mL) and ether (100 mL) were added at room temp., and the layers were separated. The aqueous layer was extracted with ether (3×100 mL), and the combined organic extracts were washed with water (100 mL), dried (Na2SO4), and concentrated under reduced pressure. The crude material (GC, Δ3:Δ2=70:30) was purified by chromatography on silica gel [200 g; pentane-Et2O (4:1); Rf=0.24 in pentane-Et2O (5:1)] and subsequent Kugelrohr distillation at 160° C./13 mbar to afford (3E)-dec-3-en-8-ynoic acid (3.79 g, 42%) as a colourless crystalline solid (mp, 40-43° C.).

1. temperatureAfter refluxing the reaction mixture for 4 h
2. customthe layers were separated
3. extractionThe aqueous layer was extracted with ether (3×100 mL)
4. washthe combined organic extracts were washed with water (100 mL)
5. dry with materialdried (Na2SO4)
6. concentrationconcentrated under reduced pressure
7. distillationThe crude material (GC, Δ3:Δ2=70:30) was purified by chromatography on silica gel [200 g; pentane-Et2O (4:1); Rf=0.24 in pentane-Et2O (5:1)] and subsequent Kugelrohr distillation at 160° C./13 mbar

ORD record

ord-b4e329234cfe484e9fd918eb584545dc

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08217185B2