Sodium hydride → 3-[4-[14-(Trimethylsilyl)tetradecylamino]benzoyl]-2,4-pentanedione

HRID 652040

Reaction equation

HRID 652040 reaction equation
[CH3:1][C:2](=[O:7])[CH2:3][C:4](=[O:6])[CH3:5].[H-].[Na+].Cl.[CH3:11][Si:12]([CH3:38])([CH3:37])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][NH:27][C:28]1[CH:36]=[CH:35][C:31]([C:32](Cl)=[O:33])=[CH:30][CH:29]=1>COCCOC>[CH3:11][Si:12]([CH3:38])([CH3:37])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][NH:27][C:28]1[CH:36]=[CH:35][C:31]([C:32]([CH:3]([C:2](=[O:7])[CH3:1])[C:4](=[O:6])[CH3:5])=[O:33])=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 31261AcetylacetoneHCID 201982304-[14-(Trimethylsilyl)tetradecylamino]benzoyl chloride hydrochloride

Product 1

HCID 201982483-[4-[14-(Trimethylsilyl)tetradecylamino]benzoyl]-2,4-pentanedione

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent3×

Procedure

A solution of 14.2 g. of 2,4-pentanedione and 20 ml. of 1,2-dimethoxyethane is added to a suspension of 6.8 g. of sodium hydride in 110 ml. of 1,2-dimethoxyethane under argon. A solution of 14.0 g. of 4-[14-(trimethylsilyl)tetradecylamino]benzoyl chloride hydrochloride in 1,2-dimethoxyethane is then added. The reaction mixture is stirred at room temperature for 12 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. The residue is then chromatographed over silica gel to yield the product as a white solid.

Workup

  1. temperaturecooled
  2. additionpoured on ice
  3. extractionextracted with ether
  4. washThe ether solution is washed with water and saturated sodium chloride solution
  5. dry with materialdried with anhydrous sodium sulfate
  6. customevaporated
  7. customThe residue is then chromatographed over silica gel

Sources & evidence

ORD record
ord-e024bcba5a4c4df882da6a6d92b9da44
Source dataset
uspto-grants-1987_06
Patent number
US04670421

Linked notes

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