Sodium hydride → tert-Butyl ethyl 4-[14-(trimethylsilyl)tetradecylamino]benzoylmalonate

HRID 652038

Reaction equation

HRID 652038 reaction equation
[C:1]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].Cl.[CH3:17][Si:18]([CH3:44])([CH3:43])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][NH:33][C:34]1[CH:42]=[CH:41][C:37]([C:38](Cl)=[O:39])=[CH:36][CH:35]=1>COCCOC>[CH3:44][Si:18]([CH3:17])([CH3:43])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][NH:33][C:34]1[CH:35]=[CH:36][C:37]([C:38]([CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:1]([O:9][C:10]([CH3:12])([CH3:11])[CH3:13])=[O:8])=[O:39])=[CH:41][CH:42]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 96345tert-Butyl ethyl malonateHCID 201982304-[14-(Trimethylsilyl)tetradecylamino]benzoyl chloride hydrochloride

Product 1

HCID 20198261tert-Butyl ethyl 4-[14-(trimethylsilyl)tetradecylamino]benzoylmalonate

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent3×

Procedure

A solution of 14 g. of tert-butyl ethyl malonate in 5 ml. of 1,2-dimethoxyethane is added to a suspension of 2.0 g. of sodium hydride in 1,2-dimethoxyethane under argon. A solution of 8.4 g. of 4-[14-(trimethylsilyl)tetradecylamino]benzoyl chloride hydrochloride in 1,2-dimethoxyethane is then added. The reaction mixture is refluxed for 5 hours, cooled, poured on ice 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. The residue is then recrystallized to yield the title compound.

Workup

  1. temperatureThe reaction mixture is refluxed for 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. customThe residue is then recrystallized

Sources & evidence

ORD record
ord-54f4189f17244ebb95eff4b73d4b956b
Source dataset
uspto-grants-1987_06
Patent number
US04670421

Linked notes

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