Hydrochloric Acid → HCID 14937509, compound

HRID 554161Notes

Reaction equation

HRID 554161 reaction equation
[C:1]([CH:3]([CH2:9][C:10](=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].[ClH:18]>O1CCCC1>[Cl:18][C:1]1[NH:2][C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 15633746Ethyl 2-cyano-4-oxo-4-phenylbutanoate

Product 1

HCID 14937509HCID 14937509, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution (60 mL) of ethyl 2-cyano-4-oxo-4-phenylbutanoate (5.0 g) in tetrahydrofuran was blown in hydrogen chloride (28 g) under ice-cooling, and the mixture was stirred at room temperature for 3 hr. Then, nitrogen was blown in to remove hydrogen chloride. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=6:1) to give the title compound as a pale-yellow solid (yield 4.24 g, 79%).

Workup

  1. temperaturecooling
  2. customto remove hydrogen chloride
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=6:1)

Sources & evidence

ORD record
ord-b304c753f05b4bcab2aed370ec3d8984
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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