Diethyl Ether → 3-(Dimethylamino)-2,2-dimethylpropyl 3-oxobutanoate
Reaction equation
[CH3:1][N:2]([CH:4](O)[C:5]([CH3:8])([CH3:7])[CH3:6])[CH3:3].[CH2:10]=[C:11]1[O:15][C:13](=[O:14])[CH2:12]1.C([O:18]CC)C>C1C=CC=CC=1>[C:13]([O:14][CH2:6][C:5]([CH3:8])([CH3:7])[CH2:4][N:2]([CH3:3])[CH3:1])(=[O:18])[CH2:12][C:11]([CH3:10])=[O:15]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
To a solution of 1.71 g of 3-(N,N-dimethylamino-2,2-dimethylpropanol (Reference: M. S. Newman et al; Journal of Medicinal chemistry, vol 15, p1003 (1972)) in 2 ml of benzene was added dropwise 1.16 g of diketene with stirring at 70° C. The mixture was stirred at 70° C. for additional 1.5 hr. Solvent was distilled off in cacuo to leave a yellowish oil. The residue was dissolved in diethyl ether and then extracted with an aqueous 2N-hydrochloric acid solution. The extracts were made alkaline with an aqueous 2N sodium hydroxide solution. The mixture was extracted with diethyl ether and then the ethereal extract was washed with a saturated aqueous sodium chloride solution, and then dried over anhydrous sodium sulfate. The solvent was distilled off to give 2.8 g of 3-(N,N-dimethylamino)-2,2-dimethylpropyl acetoacetate can oily substance. The physical properties of this compound are as follows.
Workup
- stirringThe mixture was stirred at 70° C. for additional 1.5 hr
- distillationSolvent was distilled off in cacuo
- customto leave a yellowish oil
- extractionextracted with an aqueous 2N-hydrochloric acid solution
- extractionThe mixture was extracted with diethyl ether
- extractionthe ethereal extract
- washwas washed with a saturated aqueous sodium chloride solution
- dry with materialdried over anhydrous sodium sulfate
- distillationThe solvent was distilled off
Sources & evidence
- ORD record
- ord-62a770253cc44733a35552f9442f8d4d
- Source dataset
- uspto-grants-1986_03
- Patent number
- US04578395
Reaction notes
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