Reaction equation
[CH3:1][CH:2]([C:8]([CH3:10])=[O:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].[CH2:13]1[CH2:20][O:19][S:16](=[O:18])(=[O:17])[CH2:15][CH2:14]1>CN(C)C=O>[CH2:6]([O:5][C:3]([C:2]([CH3:1])([C:8](=[O:9])[CH3:10])[CH2:20][CH2:13][CH2:14][CH2:15][S:16]([OH:19])(=[O:18])=[O:17])=[O:4])[CH3:7]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Ethyl 2-methylacetoacetate (43.2 g) in N,N-dimethylformamide (25 ml) was added to a suspension of sodium hydride (12.0 g of 60% NaH in mineral oil) in N,N-dimethylformamide (100 ml), dropwise with ice-bath cooling. This mixture was allowed to warm to ambient temperature for 30 mins before re-cooling. 1,4-butanesultone (40.8 g) in N,N-dimethylformamide (25 ml) was then added dropwise. The final mixture was heated at 50° C. for 18 hrs, then quenched with 50 ml of water. The solvent was evaporated under vacuum; the residue was partitioned between water and diethyl ether. The aqueous layer was collected, washed with fresh diethyl ether and evaporated under vacuum; final drying was under high vacuum over phosphorus pentoxide. A yield of 103 g of 5-(ethoxycarbonyl)-5-methyl-6-oxoheptane-1-sulfonic acid was obtained.
Workup
- temperaturecooling
- temperaturebefore re-cooling
- customquenched with 50 ml of water
- customThe solvent was evaporated under vacuum
- customthe residue was partitioned between water and diethyl ether
- customThe aqueous layer was collected
- washwashed with fresh diethyl ether
- customevaporated under vacuum
- customfinal drying
Sources & evidence
- ORD record
- ord-a84c320341604e82bcceda72e086f20b
- Source dataset
- uspto-grants-2011_10
- Patent number
- US08044203B2
Linked notes
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