Water → HCID 23117620, compound

HRID 1178326Notes

Reaction equation

HRID 1178326 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:9]=[C:10]([C:15]([NH:24][CH:25]=O)([CH2:21][CH:22]=[CH2:23])[C:16](OCC)=[O:17])[CH:11]=[CH:12][C:13]=1[Cl:14].O.[OH-].[Na+]>O1CCCC1>[ClH:7].[Cl:7][C:8]1[CH:9]=[C:10]([C:15]([NH:24][CH3:25])([CH2:21][CH:22]=[CH2:23])[CH2:16][OH:17])[CH:11]=[CH:12][C:13]=1[Cl:14]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 23117566HCID 23117566, compound

Product 1

HCID 23117620HCID 23117620, compoundYield 166%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under argon flow, lithium aluminum hydride (78 g) was suspended in dehydrated tetrahydrofuran (1 L). Ethyl 2-(3,4-dichlorophenyl)-2-formylamino-4-pentenoate (334 g) in dehydrated tetrahydrofuran (1 L) was added to the suspension at room temperature, followed by refluxing for 15 minutes. After the mixture was cooled with ice, water (78 mL), 15% aqueous sodium hydroxide (78 mL), and then water (234 mL) were added to the mixture, and the resultant mixture was stirred at room temperature for one hour. The insoluble matter was passed through Celite, followed by washing with ethyl acetate. The filtrate was dried over magnesium sulfate anhydrate and concentrated under reduced pressure until the volume of the solution was decreased to 1 L. 4N HCl-1,4-dioxane (260 mL) was added to the residue, and the mixture was concentrated under reduced pressure. Ethyl acetate was added to the residue, followed by filtration and drying, to thereby give the title compound (260 g, 69%, 5 steps).

Workup

  1. temperatureby refluxing for 15 minutes
  2. washby washing with ethyl acetate
  3. dry with materialThe filtrate was dried over magnesium sulfate anhydrate
  4. concentrationconcentrated under reduced pressure until the volume of the solution
  5. addition4N HCl-1,4-dioxane (260 mL) was added to the residue
  6. concentrationthe mixture was concentrated under reduced pressure
  7. additionEthyl acetate was added to the residue
  8. filtrationfollowed by filtration
  9. customdrying

Sources & evidence

ORD record
ord-dc67603275874563923d2b6bca796cc4
Source dataset
uspto-grants-2007_10
Patent number
US07276511B2

Reaction notes

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