Ethyl Acetate → HCID 22636246, compound

HRID 1662013Notes

Reaction equation

HRID 1662013 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[F:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][NH:15][C:16](OCC)=O)=[CH:10][CH:9]=1.CCOC(C)=O>C1COCC1>[F:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][NH:15][CH3:16])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 12926196HCID 12926196, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 22636246HCID 22636246, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

To a mixture of LiAlH4 (1.1 g) in THF (15 mL) is added a solution of ethyl 2-(4-fluorophenyl)hydrazinecarboxylate (1.9 g, 9.59 mmol) in THF (10 mL) dropwise under nitrogen in an ice-salt bath. After the addition, the ice bath is removed and the mixture is heated to 60° C. overnight. The reaction is cooled and quenched with water. The precipitate is filtered and washed with EtOAc. The organic phase is separated, dried over Na2SO4, and concentrated. The residue is purified by flash chromatography, eluting with PE:EtOAc (80:1 to 60:1) to afford the title compound (1 g, 74% yield). MS (m/z): 141 (M+H).

Workup

  1. additionAfter the addition
  2. customthe ice bath is removed
  3. temperatureThe reaction is cooled
  4. customquenched with water
  5. filtrationThe precipitate is filtered
  6. washwashed with EtOAc
  7. customThe organic phase is separated
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated
  10. customThe residue is purified by flash chromatography
  11. washeluting with PE

Sources & evidence

ORD record
ord-def9faf62545479fb67b17bad0331288
Source dataset
uspto-grants-2011_10
Patent number
US08030302B2

Reaction notes

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