Ethyl 5-(3-chlorophenyl)-3-oxopentanoate → HCID 178472912, compound

HRID 324442Notes

Reaction equation

HRID 324442 reaction equation
[N:1]([O-:3])=O.[Na+].[Cl:5][C:6]1[CH:7]=[C:8]([CH2:12][CH2:13][C:14](=[O:21])[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:9]=[CH:10][CH:11]=1>O.C(O)(=O)C>[Cl:5][C:6]1[CH:7]=[C:8]([CH2:12][CH2:13][C:14](=[O:21])[C:15](=[N:1][OH:3])[C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 20462750Ethyl 5-(3-chlorophenyl)-3-oxopentanoateHCID 23668193Sodium Nitrite

Product 1

HCID 178472912HCID 178472912, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

A solution of sodium nitrite (12.6 g) in water (25 ml) was added to a stirred solution of the product from step (i) (42.2 g) in acetic acid (50 ml) at <30° C. The reaction mixture was stirred at room temperature for 30 min. Water (75 ml) was added and the mixture was stirred for 2 hours and extracted with diethyl ether. The combined extracts were washed with water and saturated aqueous sodium bicarbonate solution. The organic layer was collected, dried (MgSO4) and solvent evaporated under reduced pressure to give the subtitle product.

Workup

  1. stirringthe mixture was stirred for 2 hours
  2. extractionextracted with diethyl ether
  3. washThe combined extracts were washed with water and saturated aqueous sodium bicarbonate solution
  4. customThe organic layer was collected
  5. dry with materialdried (MgSO4) and solvent
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-61537318b33e4322bf69b4ce6c7e7df2
Source dataset
uspto-grants-2001_04
Patent number
US06218376B1

Reaction notes

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