Ethyl bromoacetate → Ethyl 4-oxo-3-propanoylhexanoate
Reaction equation
[H-].[Na+].[CH3:3][CH2:4][C:5](=[O:11])[CH2:6][C:7](=[O:10])[CH2:8][CH3:9].[CH2:12]([O:14][C:15](=[O:18])[CH2:16]Br)[CH3:13].[Cl-].[NH4+]>O1CCCC1>[CH2:12]([O:14][C:15](=[O:18])[CH2:16][CH:6]([C:5](=[O:11])[CH2:4][CH3:3])[C:7](=[O:10])[CH2:8][CH3:9])[CH3:13]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a suspension of sodium hydride (5.2 g, 130 mmol, 60% in mineral oil) in tetrahydrofuran (100 mL) at 0° C. was added dropwise a solution of heptane-3,5-dione (16.6 g, 130 mmol) in tetrahydrofuran (30 mL). After 15 minutes, bromo-acetic acid ethyl ester (14.4 mL, 130 mmol) was added and the reaction mixture was stirred for 16 h at room temperature. The reaction mixture was poured into an aqueous ammonium chloride solution and extracted several times with ethyl acetate. The combined ethyl acetate layers were washed with water and a saturated aqueous solution of sodium chloride, dried over sodium sulfate, and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (0-30% ethyl acetate in heptane) to obtain 4-oxo-3-propionyl-hexanoic acid ethyl ester (19 g, 68%) as yellow oil.
Workup
- extractionextracted several times with ethyl acetate
- washThe combined ethyl acetate layers were washed with water
- dry with materiala saturated aqueous solution of sodium chloride, dried over sodium sulfate
- concentrationconcentrated under reduced pressure
- customThe crude product was purified by silica gel column chromatography (0-30% ethyl acetate in heptane)
Sources & evidence
- ORD record
- ord-4262a5a49c1746139904f87367df722e
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07943652B2
Reaction notes
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