Diisopropylamine → HCID 131715944, compound

HRID 1761974Notes

Reaction equation

HRID 1761974 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[C:13]([O:19][CH2:20][CH3:21])(=[O:18])[CH2:14][C:15]([CH3:17])=[O:16].[F:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[C:30]([CH:43]=[CH:44][CH:45]=[O:46])=[C:31]([CH:40]([CH3:42])[CH3:41])[S:32][C:33]=2[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[CH:25][CH:24]=1>C1COCC1>[F:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[C:30]([CH:43]=[CH:44][CH:45]([OH:46])[CH2:17][C:15](=[O:16])[CH2:14][C:13]([O:19][CH2:20][CH3:21])=[O:18])=[C:31]([CH:40]([CH3:42])[CH3:41])[S:32][C:33]=2[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 7912DiisopropylamineHCID 8868Ethyl AcetoacetateHCID 131715943HCID 131715943, compoundHCID 178418339Butyllithium

Product 1

HCID 131715944HCID 131715944, compoundYield 121.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of 2.6 g of diisopropylamine in 30 ml of THF at 0° was added 1.67 g of n-butyllithium (1.16 m in hexane). Then a solution of 1.7 g of ethyl acetoacetate in 10 ml of THF was added dropwise. After stirring at 0° for 1 hour, the mixture was cooled to -20°, then a solution of 3.3 g of the title product of Step 3, above, in 20 ml of THF was added dropwise. The reaction was stirred at -20° for 1 hour. Then was quenched with saturated aqueous ammonium chloride solution. The mixture was extracted with MTBE and then methylene chloride and the organic solutions were combined and dried, adn the solvent evaporated under reduced pressure to give 5.5 g of crude title product of this step as an oil. This was used without further purification in the next step (Step 5).

Workup

  1. temperaturethe mixture was cooled to -20°
  2. stirringThe reaction was stirred at -20° for 1 hour
  3. customThen was quenched with saturated aqueous ammonium chloride solution
  4. extractionThe mixture was extracted with MTBE
  5. customdried, adn the solvent
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-81ba58a3660044caaa759011b6685a0b
Source dataset
uspto-grants-1989_05
Patent number
US04829081

Reaction notes

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