Ethyl 2-methylacetoacetate → HCID 57614922, compound
Reaction equation
[H-].[Na+].C(O[C:6](=O)[CH:7](C)[C:8]([CH3:10])=[O:9])C.[CH2:13]1[CH2:19][S:16](=[O:18])(=[O:17])[O:15][CH2:14]1>C1COCC1>[CH3:6][CH:7]([C:8](=[O:9])[CH3:10])[CH2:14][CH2:13][CH2:19][S:16]([OH:15])(=[O:18])=[O:17]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Sodium hydride (2.1 g, 80 wt %=69 mmol) was slurried in 10 ml dry THF. The suspension was cooled to 0° C. and a solution of ethyl-2-methylacetoacetate (10 g, 69 mmol) in 10 ml dry THF was added dropwise. The solution was stirred at room temperature for one h. A solution of 1,3-propanesultone (8.42 g, 69 mmol) in 10 ml dry THF was added dropwise. Once the addition was complete, the solution was stirred for two h at 40° C. The solution was evaporated to dryness. The residue was dissolved in 100 ml water. The aqueous solution was extracted twice with ethylacetate, then 100 ml concentrated HCl was added and the solution was refluxed for two hours. The solvent was evaporated in vacuum. The residue was purified by column chromatography (silica, methanol/dichloromethane) to give 4-methyl-5-oxohexane sulfonic acid. Yield 10 g; MS (ESI−): 193.2 [M]−
Workup
- additionOnce the addition
- stirringthe solution was stirred for two h at 40° C
- customThe solution was evaporated to dryness
- dissolutionThe residue was dissolved in 100 ml water
- extractionThe aqueous solution was extracted twice with ethylacetate
- addition100 ml concentrated HCl was added
- temperaturethe solution was refluxed for two hours
- customThe solvent was evaporated in vacuum
- customThe residue was purified by column chromatography (silica, methanol/dichloromethane)
Sources & evidence
- ORD record
- ord-9fc0663ecad5424b98bc57056aea8a28
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08889884B1
Reaction notes
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