2-Methoxyethanol → HCID 86708329, compound

HRID 402635Notes

Reaction equation

HRID 402635 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.ClCC(=O)C[C:23]([O:25][CH3:26])=O.FC1C=CC(N=C=O)=CC=1.COCCO>O1CCOCC1.[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][CH2:23][O:25][CH3:26])=[O:15])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 80192-MethoxyethanolHCID 36240Methyl 4-chloroacetoacetateHCID 709554-Fluorophenyl isocyanateHCID 86708321HCID 86708321, compound

Product 1

HCID 86708329HCID 86708329, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

A solution of methyl 2-[(4-fluorophenyl)amino]-4-oxo-4,5-dihydrofuran-3-carboxylate (0.063 g, 0.25 mmol) which similarly prepared according to the procedure described in the Example 2, First step using methyl 4-chloroacetoacetate and 4-fluorophenyl isocyanate, 2-methoxyethanol (0.2 mL, 2.5 mmol) and zinc cluster catalyst (Zn4(OCOCF3)6O) (0.0048 g, 0.0050 mmol) in anhydrous dioxane (1.0 mL) was stirred with the microwave synthesizer (Biotage Initiator™) at 120° C. for 1 h. Cooled to ambient temperature, the reaction mixture was concentrated under reduced pressure. The residue was purified by chromatography on silica gel(chloroform/ethyl acetate) to afford 2-methoxyethyl 2-[(4-fluorophenyl)amino]-4-oxo-4,5-dihydrofuran-3-carboxylate as solid (0.024 g, y. 33%).

Workup

  1. temperatureCooled to ambient temperature
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customThe residue was purified by chromatography on silica gel(chloroform/ethyl acetate)

Sources & evidence

ORD record
ord-91aa5ecd0d80442690412c7b651a85d8
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

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