Diethyl Malonate → Diethyl 4-[14-(trimethylsilyl)tetradecylamino]benzoylmalonate

HRID 652037

Reaction equation

HRID 652037 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].Cl.[CH3:15][Si:16]([CH3:42])([CH3:41])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][NH:31][C:32]1[CH:40]=[CH:39][C:35]([C:36](Cl)=[O:37])=[CH:34][CH:33]=1>COCCOC>[CH3:42][Si:16]([CH3:15])([CH3:41])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][NH:31][C:32]1[CH:33]=[CH:34][C:35]([C:36]([CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:1]([O:9][CH2:10][CH3:11])=[O:8])=[O:37])=[CH:39][CH:40]=1

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 201982304-[14-(Trimethylsilyl)tetradecylamino]benzoyl chloride hydrochloride

Product 1

HCID 20198253Diethyl 4-[14-(trimethylsilyl)tetradecylamino]benzoylmalonate

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent3×

Procedure

A solution of 26.6 g. of diethyl malonate and 10 ml. of 1,2-dimethoxyethane is added to a suspension of 4.0 g. of sodium hydride in 1,2-dimethoxyethane under argon. A solution of 16.9 g. of 4-[14-(trimethylsilyl)tetradecylamino]benzoyl chloride hydrochloride in 1,2-dimethoxyethane is then added. The reaction mixture is refluxed for 4.5 hours, cooled, poured on ice, acidified, and extracted with ether. The ether solution is washed with water and saturated sodium chloride solution, dried with anhydrous sodium sulfate and evaporated to dryness. Addition of a small amount of ethanol to the residue gives a solid which is filtered and discarded. The ethanol filtrate is evaporated and the residue is recrystallized to yield the title product.

Workup

  1. temperatureThe reaction mixture is refluxed for 4.5 hours
  2. temperaturecooled
  3. additionpoured on ice
  4. extractionextracted with ether
  5. washThe ether solution is washed with water and saturated sodium chloride solution
  6. dry with materialdried with anhydrous sodium sulfate
  7. customevaporated to dryness
  8. additionAddition of a small amount of ethanol to the residue
  9. customgives a solid which
  10. filtrationis filtered
  11. customThe ethanol filtrate is evaporated
  12. customthe residue is recrystallized

Sources & evidence

ORD record
ord-ae6f7d9d6bdc4bbc9260b5b9a582def7
Source dataset
uspto-grants-1987_06
Patent number
US04670421

Linked notes

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