Hydrochloric Acid → HCID 14235018, compound

HRID 622382Notes

Reaction equation

HRID 622382 reaction equation
[CH2:1]([O:3][C:4](=[O:9])[CH2:5][C:6]([OH:8])=O)[CH3:2].C([Li])CCC.[CH3:15][N:16]([CH3:30])[C:17]1[C:25]([F:26])=[C:24]([F:27])[C:23]([F:28])=[C:22]([F:29])[C:18]=1C(Cl)=O.C(O[Li])(=O)CC(O[Li])=O.Cl>C1COCC1.O>[CH3:15][N:16]([CH3:30])[C:17]1[C:25]([F:26])=[C:24]([F:27])[C:23]([F:28])=[C:22]([F:29])[C:18]=1[C:6](=[O:8])[CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:9]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 70615Monoethyl malonateHCID 14235017HCID 14235017, compoundHCID 178418339Butyllithium2×HCID 178506950HCID 178506950, compound

Product 1

HCID 14235018HCID 14235018, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4.76 g (36 mmol) of malonic acid monoethyl ester and 75 ml of THF at -35° was added 25 ml (40 mmol) of 1.5N n-butyl lithium solution. The remaining 25 ml (40 mmol) of 1.5N butyllithium solution was added at 0°. After cooling to -78°, a solution of the 4.8 g of 2-(dimethylamino)-3,4,5,6-tetrafluorobenzoyl chloride in 50 ml of THF was added to the dilithio malonate over a 15 minute period. The reaction mixture was stirred for 1.75 hours while the temperature came up to -30°. The reaction mixture was poured into ice, water, and 50 ml of 1N HCl. The mixture was extracted with ether and the ether extract was washed with H2O, 5% NaHCO3, and HCl. After drying over MgSO4 the ether solution was concentrated to 4.4 g of oily product. NMR spectra indicated the desired product.

Workup

  1. temperatureAfter cooling to -78°
  2. customcame up to -30°
  3. extractionThe mixture was extracted with ether
  4. extractionthe ether extract
  5. washwas washed with H2O, 5% NaHCO3, and HCl
  6. dry with materialAfter drying over MgSO4 the ether solution
  7. concentrationwas concentrated to 4.4 g of oily product

Sources & evidence

ORD record
ord-bfab3c85c7a6498382e3654b028ef638
Source dataset
uspto-grants-1988_09
Patent number
US04771055

Reaction notes

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