Reaction equation
[O:1]=[C:2]([CH2:7][CH3:8])[CH2:3][C:4]([OH:6])=[O:5].Cl>C1COCC1>[CH2:7]([C:2]1[O:5][C:4](=[O:6])[C:3]([C:2](=[O:1])[CH2:7][CH3:8])=[C:4]([OH:5])[CH:3]=1)[CH3:8]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
3-Oxopentanoic acid (II in Scheme 1; Example 1.1; 2 g; 17.2 mmol) was dissolved in 30 ml THF and cooled to 0° C. To the solution, was added dicarbodiimidazole (3.6 g; 22.2 mmol; Aldrich). The reaction mixture was stirred for 18 h at 25° C., neutralized with 2% HCl, extracted with 3×30 ml EtOAc, dried with anhydrous Na2SO4, and evaporated to a white solid. The product was purified via silica chromatography (20% EtOAc in hexanes).
Workup
- additionTo the solution, was added dicarbodiimidazole (3.6 g; 22.2 mmol; Aldrich)
- extractionextracted with 3×30 ml EtOAc
- dry with materialdried with anhydrous Na2SO4
- customevaporated to a white solid
- customThe product was purified via silica chromatography (20% EtOAc in hexanes)
Sources & evidence
- ORD record
- ord-87569190479a43878ef0475ad79800cb
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09187446B2
Linked notes
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