Ethanol → Diethyl 2-acetylamino-2-(3,4-diethyl-benzyl)-malonate
Reaction equation
[Na].CCO.[C:5]([NH:8][CH:9]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11])(=[O:7])[CH3:6].Br[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH3:29])=[C:24]([CH2:30][CH3:31])[CH:23]=1>O1CCOCC1>[C:5]([NH:8][C:9]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH3:29])=[C:24]([CH2:30][CH3:31])[CH:23]=1)([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11])(=[O:7])[CH3:6]Participants
Procedure
Under a nitrogen atmosphere 8.14 g (354 mmol) of sodium was added in batches to 200 mL abs. EtOH and stirred until fully dissolved. 76.9 g (354 mmol) diethyl 2-acetylaminomalonate was then added to this solution, whereupon the sodium salt formed was precipitated. After the addition of 150 mL 1,4-dioxane a solution of 80 g (352 mmol) of 4-bromomethyl-1,2-diethyl-benzene in 500 mL of 1,4-dioxane was added dropwise to this suspension. The reaction solution was kept at 50° C. for 2 hours and then stirred for 16 hours at RT. The solvent was distilled off i. vac., the oily residue was combined with water, while the product was obtained in the form of white crystals. These were suction filtered, washed with water and reacted without any further purification.
Workup
- dissolutionuntil fully dissolved
- customformed
- customwas precipitated
- additionwas added dropwise to this suspension
- distillationThe solvent was distilled off i
- customwas obtained in the form of white crystals
- washThese were suction filtered, washed with water
- customreacted without any further purification
Sources & evidence
- ORD record
- ord-85c3bad978cd41068f67d5e1465efb88
- Source dataset
- uspto-grants-2006_04
- Patent number
- US07026312B2
Reaction notes
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