Methyl 4-chloroacetoacetate → HCID 86708322, compound

HRID 402629Notes

Reaction equation

HRID 402629 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[O:10][CH2:11][C:12](=[O:18])[C:13]=2[C:14]([O:16][CH3:17])=[O:15])=[CH:4][CH:3]=1.Cl[CH2:20][C:21](=O)[CH2:22]C(OC)=O.FC1C=CC(N=C=O)=CC=1>C(O)CCC.[Zn]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]2[O:10][CH2:11][C:12](=[O:18])[C:13]=2[C:14]([O:16][CH2:17][CH2:20][CH2:21][CH3:22])=[O:15])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 36240Methyl 4-chloroacetoacetateHCID 709554-Fluorophenyl isocyanateHCID 86708321HCID 86708321, compound

Product 1

HCID 86708322HCID 86708322, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 2631-ButanolSolvent

Conditions

Temperature
80 °C

Procedure

Under a nitrogen atmosphere, a solution of methyl 2-[(4-fluorophenyl)amino]-4-oxo-4,5-dihydrofuran-3-carboxylate (0.13 g, 0.50 mmol) which similarly prepared according to the procedure described in the Example 2, First step using methyl 4-chloroacetoacetate and 4-fluorophenyl isocyanate, and zinc cluster catalyst (Zn4(OCOCF3)6O) (0.0062 g, 0.0065 mmol) in 1-butanol (2.0 mL) was stirred at 80° C. for 3 days then stirred at ambient temperature for further 3 days. The precipitate was collected by filtration, washed with 2-propanol and diisopropyl ether then dried to afford n-butyl 2-[(4-fluorophenyl)amino]-4-oxo-4,5-dihydrofuran-3-carboxylate as solid (0.078 g, y. 53%).

Workup

  1. stirringthen stirred at ambient temperature for further 3 days
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with 2-propanol and diisopropyl ether
  4. customthen dried

Sources & evidence

ORD record
ord-bf6531f847e54966a7519770df7745bc
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

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