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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
Synonyms: 4-Acetylbutyric acid; 5-Oxohexanoic acid; NSC-5281
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| CAS No. : | 3128-06-1 |
| Formula : | C6H10O3 |
| M.W : | 130.14 |
| SMILES Code : | O=C(O)CCCC(C)=O |
| Synonyms : |
4-Acetylbutyric acid; 5-Oxohexanoic acid; NSC-5281
|
| English Name : | 4-Acetylbutyric acid |
| MDL No. : | MFCD00004412 |
| InChI Key : | MGTZCLMLSSAXLD-UHFFFAOYSA-N |
| Pubchem ID : | 18407 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 92%Chromat. | In water; at 160℃; for 4h;Sealed tube; | 2 mmol of acetylbutyric acid, 10 mmol of formamide and 40 mmol of water were placed in a 15 mL polytetrafluoroethylene-lined stainless steel reaction vessel.The sealed reaction kettle is placed in an oil bath that has been heated to a predetermined temperature (160 C). The reaction was carried out at 500 r/min for 240 min. The reaction vessel was taken out and cooled to room temperature with tap water. Add 13 mL of methanol to the reaction kettle.The yield of 6-methyl-2-piperidone was determined by GC,The conversion of acetylbutyrate was measured by HPLC. Using naphthalene as an internal standard to make a standard curve, The yield of 6-methyl-2-piperidone (m/z: 113.1) in the reaction mixture was determined by gas chromatography to be 92%. The conversion of acetobutyrate was determined by liquid chromatography to be 100%. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 92% | With (dipyridylamine)Cp*IrOSO3; hydrogen In water at 130℃; for 32h; | |
| 84% | With 1,2-bis(dimethylsilyl)ethane; tris(pentafluorophenyl)borate In dichloromethane at 20℃; for 0.166667h; Inert atmosphere; | 2.3 General procedure to synthesize lactones from keto acids. General procedure: To a solution of levulinic acid (LA) (40 mg, 0.34 mmol) and (HMe2SiCH2)2 (55mg, 0.38 mmol) in anhydrous CH2Cl2 (4 mL) under argon atmosphere was addedB(C6F5)3 (1.8 mg, 0.0035 mmol) at room temperature. The resulting mixture wasstirred at the same temperature for 10 min before quenching with H2O (2 mL) andextraction with CH2Cl2 (3 × 3 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure. Purification of the crudeproduct by silica gel flash column chromatography (gradient eluent: 0-3% ofEtOAc/petroleum ether) afforded GVL (29 mg, 86% yield) as a colorless oil. |
| 78% | With sodium tetrahydroborate In water at 10 - 20℃; for 2h; |
| 60% | With Pt/TiO2 In isopropyl alcohol at 110℃; for 24h; Inert atmosphere; | |
| 40% | With sodium tetrahydroborate In tetrahydrofuran; water at 150℃; for 2h; Microwave irradiation; Green chemistry; | |
| 22% | With sodium tetrahydroborate; boric buffer for 12h; bivine serum albumin, pH 10.0; | |
| With sodium hydroxide; sodium amalgam anschliessend Ansaeuern; | ||
| With diethyl ether at 60℃; Hydrogenation; | ||
| Multi-step reaction with 3 steps 1.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide / dichloromethane / 0.17 h / 20 °C 2.1: sodium tetrahydroborate / methanol; diethyl ether; water / 20 °C 3.1: acetonitrile / 0.08 h 3.2: 6 h / 20 °C | ||
| 82 %Spectr. | With C12H14N4*Ir(1+)*2CO*BF4(1-)*C3H7NO; hydrogen; potassium hydroxide In isopropyl alcohol at 100℃; for 24h; Autoclave; | |
| > 99 %Spectr. | With hydrogen; potassium hydroxide In isopropyl alcohol at 100℃; for 24h; Schlenk technique; Green chemistry; |

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With sodium tetrahydroborate |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 85% | In perchloric acid at 20℃; for 65h; | Intermediate S-7 A: tert-Buty1 5-oxohexanoate To a solution of 5-oxohexanoic acid (25 g, 192 mmol) in t-butyl acetate (600mL) was added perchloric acid (500 )lL, 8.31 mmol) and the resulting pale yellowsolution was allowed to stir at room temp, with a drying tube in place, for 65 h. Thereaction was diluted with ethyl acetate ( 400 mL) and then quenched with a mixture of20 sodium bicarbonate (50 g, 595 mmol) and water (100 mL). The organic layer wasextracted with saturated aqueous sodium bicarbonate (5 x 150 mL), water (1 x 100 mL),brine (1 x 75 mL), dried over sodium sulfate, and filtered. The solvent was removed invacuo to give the title compound (30.55 g, 85%) as a light oil. 1H NMR (500MHz,chloroform-d) 8 2.50 (t, J=7.2 Hz, 2H), 2.25 (t, J=7.3 Hz, 2H), 2.16 (s, 3H), 1.89-1.83 (m,25 2H), 1.46 (s, 9H). |
| With perchloric acid for 24h; Ambient temperature; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With sodium methylate In methanol for 6h; electrolysis between Pt electrodes; Yield given; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 74% | With sulfuric acid Ambient temperature; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 58% | With dmap; dicyclohexyl-carbodiimide In dichloromethane for 40h; | |
| With dicyclohexyl-carbodiimide In dichloromethane for 24h; Ambient temperature; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 80% | With magnesium diethoxide; 1,1'-carbonyldiimidazole In tetrahydrofuran for 18h; | |
| 78% | Stage #1: 5-ketohexanoic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran at 20℃; for 6h; Inert atmosphere; Stage #2: hydrogen ethyl malonate With magnesium diethoxide In tetrahydrofuran at 20℃; for 18h; Inert atmosphere; | |
| 67% | Stage #1: 5-ketohexanoic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran at 20℃; for 6h; Stage #2: hydrogen ethyl malonate With magnesium diethoxide In tetrahydrofuran at 20℃; for 18h; |