Malonic Acid → HCID 54076284, compound

HRID 1461142Notes

Reaction equation

HRID 1461142 reaction equation
[C:1]1([C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:11](=[O:14])[CH2:12][CH3:13])[CH2:8]C=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:21](O)(=O)[CH2:22][C:23]([OH:25])=[O:24]>N1C=CC=CC=1>[C:1]1([C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:11](=[O:14])[CH2:12][CH3:13])[CH:8]=[CH:21][CH2:22][C:23]([OH:25])=[O:24])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 867Malonic AcidHCID 19981497HCID 19981497, compound

Product 1

HCID 54076284HCID 54076284, compoundYield 72.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 3,3-diphenyl-4-oxo-hexanal (45 mg)[from Example 2], malonic acid (40 mg) and pyridine (1.5 ml) was heated at 80°-90° C. for 18 hours, with stirring. The volatiles were removed in vacuo and the residue was partitioned between water and chloroform (3×). The combined extracts were washed with water and dried (Na2SO4). Rotary evaporation of the solution gave a crude material which was purified by PTLC. Development with hexane/ethyl acetate (2:1) produced two bands. The lower band which was near the origin was scraped off the plate and eluted with methanol. Rotary evaporation of the solution yielded 38 mg of 5,5-diphenyl-6-oxo-3-octenoic acid.

Workup

  1. temperaturewas heated at 80°-90° C. for 18 hours
  2. customThe volatiles were removed in vacuo
  3. customthe residue was partitioned between water and chloroform (3×)
  4. washThe combined extracts were washed with water
  5. dry with materialdried (Na2SO4)
  6. customRotary evaporation of the solution
  7. customgave a crude material which
  8. customwas purified by PTLC
  9. customDevelopment with hexane/ethyl acetate (2:1) produced two bands
  10. washeluted with methanol
  11. customRotary evaporation of the solution

Sources & evidence

ORD record
ord-96e56c6867bc4c10a0dcbe439b82b807
Source dataset
uspto-grants-1991_12
Patent number
US05073629

Reaction notes

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