Sodium Nitrite → HCID 178472910, compound

HRID 324424Notes

Reaction equation

HRID 324424 reaction equation
[N:1]([O-:3])=O.[Na+].[CH3:5][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>[OH:3][N:1]=[C:15]([C:14](=[O:21])[CH2:13][CH2:12][C:8]1[CH:9]=[CH:10][CH:11]=[C:6]([CH3:5])[CH:7]=1)[C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

5

Reactant 2

HCID 23668193Sodium NitriteHCID 54309110Ethyl 3-oxo-5-m-toluylpentanoate

Product 1

HCID 178472910HCID 178472910, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

Sodium nitrite (32 g) in water (60 ml) was added dropwise over 1 hour to a stirred solution of the product from example 13 step (i) (99.4 g) in acetic acid (200 ml) at a rate such that the internal temperature did not rise above 30° C. The solution was allowed to stir a further 1 hour before adding water (500 ml). After stirring for a further 24 h the reaction mixture was extracted with diethyl ether (×4). The combined ether extracts were washed with saturated sodium bicarbonate solution, and finally water before collecting the organic layer and drying over magnesium sulphate. The solution was filtered and the solvent evaporated under reduced pressure to leave the subtitle product.

Workup

  1. customdid not rise above 30° C
  2. stirringAfter stirring for a further 24 h the reaction mixture
  3. extractionwas extracted with diethyl ether (×4)
  4. washThe combined ether extracts were washed with saturated sodium bicarbonate solution, and finally water
  5. custombefore collecting the organic layer
  6. dry with materialdrying over magnesium sulphate
  7. filtrationThe solution was filtered
  8. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-9cf04f13af854fc48aded8d0d453957a
Source dataset
uspto-grants-2001_04
Patent number
US06218376B1

Reaction notes

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