Ethanol → Diethyl 2-acetylamino-2-(3,4-diethyl-benzyl)-malonate

HRID 644310Notes

Reaction equation

HRID 644310 reaction equation
[Na].[CH3:2][CH2:3]O.[C:5]([NH:8][CH:9]([C:15]([O-:17])=[O:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11])(=[O:7])[CH3:6].Br[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH3:27])=[C:22]([CH2:28][CH3:29])[CH:21]=1>O>[C:5]([NH:8][C:9]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH3:27])=[C:22]([CH2:28][CH3:29])[CH:21]=1)([C:15]([O:17][CH2:2][CH3:3])=[O:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11])(=[O:7])[CH3:6]

Participants

6

Reactant 4

HCID 702EthanolHCID 5360545SodiumHCID 153948524-(Bromomethyl)-1,2-diethylbenzeneHCID 234615602-Acetamido-3-ethoxy-3-oxopropanoate

Product 1

HCID 22184624Diethyl 2-acetylamino-2-(3,4-diethyl-benzyl)-malonate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6.7 g (0.29 mol) sodium were added to 300 mL EtOH under an argon atmosphere. 60.0 g (0.27 mol) ethyl acetamidomalonate were added to the resulting solution, stirred for 1.5 h and then 62.0 g (0.27 mol) 4-bromomethyl-1,2-diethyl-benzene were slowly added dropwise. The reaction mixture was stirred overnight at RT, poured onto 1 L of water and vigorously stirred for 1 h at RT. The precipitate formed was suction filtered, suspended twice with a little water, suction filtered and dried.

Workup

  1. stirringThe reaction mixture was stirred overnight at RT
  2. stirringvigorously stirred for 1 h at RT
  3. customThe precipitate formed
  4. filtrationfiltered
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-28f7d3bd6192457d81efab7ea607686c
Source dataset
uspto-grants-2010_04
Patent number
US07700589B2

Reaction notes

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