Water → HCID 178500902, compound

HRID 50100

Reaction equation

HRID 50100 reaction equation
[C:1]([CH2:6][C:7]([O:9][CH3:10])=[O:8])(=[O:5])[CH:2]([CH3:4])[CH3:3].[F:11][C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=1.[Sn](Cl)(Cl)(Cl)Cl.O>C1(C)C=CC=CC=1.C(OCC)(=O)C>[NH2:17][C:16](=[C:6]([C:1](=[O:5])[CH:2]([CH3:4])[CH3:3])[C:7]([O:9][CH3:10])=[O:8])[C:15]1[CH:18]=[CH:19][C:12]([F:11])=[CH:13][CH:14]=1

Participants

7

Reactant 4

HCID 962WaterHCID 145174-FluorobenzonitrileHCID 24287Tin tetrachlorideHCID 2759969Methyl 4-methyl-3-oxopentanoate

Product 1

HCID 178500902HCID 178500902, compoundYield 54.3%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
80 °C

Procedure

1.50 g of methyl isobutyrylacetate (10.0 mmol, concentration 96%) and 1.24 g of 4-fluorobenzonitrile (10 mmol, concentration 98%) were dissolved in 10 ml of toluene and treated with 2.63 g of tin tetrachloride (10 mmol, concentration 99%) at room temperature over the course of 6 min. After 3 h at room temperature, the mixture was heated to 80° C. After 2.5 h, the suspension was again cooled to room temperature and treated with 10 ml of water. It was diluted with 5 ml of ethyl acetate and the phases were separated. After extraction of the aqueous phase with ethyl acetate (2×5 ml), the combined organic phases were dried over magnesium sulphate. After concentration in vacuo, 3.50 g of crude product were obtained in the form of a pale yellow, tacky solid. The solid was dissolved in ethyl acetate and purified by flash chromatography (n-hexane/ethyl acetate 5:1 to 1:1). After concentration in vacuo, 1.44 g of methyl 2-[1-amino-1-(4-fluorophenyl)-methylene]-4-methyl-3-oxopentanoate were obtained.

Workup

  1. waitAfter 2.5 h
  2. temperaturethe suspension was again cooled to room temperature
  3. customthe phases were separated
  4. extractionAfter extraction of the aqueous phase with ethyl acetate (2×5 ml)
  5. dry with materialthe combined organic phases were dried over magnesium sulphate
  6. concentrationAfter concentration in vacuo
  7. custom3.50 g of crude product were obtained in the form of a pale yellow, tacky solid
  8. custompurified by flash chromatography (n-hexane/ethyl acetate 5:1 to 1:1)
  9. concentrationAfter concentration in vacuo

Sources & evidence

ORD record
ord-f708f937c0bb4b5491440975fa798452
Source dataset
uspto-grants-2004_03
Patent number
US06710178B2

Linked notes

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