Formaldehyde → HCID 67256194, compound

HRID 873510Notes

Reaction equation

HRID 873510 reaction equation
[O:1]1[CH2:5]CCC1.C=O.[C:8](=O)([O-])[O-:9].[K+].[K+].[CH3:14][O:15][C:16]([C:18]1([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)[CH2:22][CH2:21][CH2:20][C:19]1=[O:23])=[O:17]>O>[CH3:14][O:15][C:16]([C:18]1([CH2:24][C:25]2[CH:26]=[CH:27][C:28]([Cl:31])=[CH:29][CH:30]=2)[CH2:22][CH2:21][C:20]([CH2:5][OH:1])([CH2:8][OH:9])[C:19]1=[O:23])=[O:17]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 4204026HCID 4204026, compound

Product 1

HCID 67256194HCID 67256194, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Tetrahydrofuran (0.72 ml), a 37% formaldehyde aqueous solution (0.242 ml), and potassium carbonate (0.50 mmol) were added to 1-(4-chlorobenzyl)-2-oxocyclopentanecarboxylic acid methyl ester (Compound VI-1) (1.0 mmol), and the mixture was allowed to react at room temperature for 5 hours. Water was added to the resultant reaction solution, and the resultant reaction solution was extracted with ethyl acetate. The organic layer was washed with saturated brine, and thereafter dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified with the use of a silica gel column. In this way, Compound V-1 was obtained.

Workup

  1. customto react at room temperature for 5 hours
  2. customreaction solution
  3. customthe resultant reaction solution
  4. extractionwas extracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off
  8. customthe residue was purified with the use of a silica gel column
  9. customIn this way, Compound V-1 was obtained

Sources & evidence

ORD record
ord-edd513daf82746358a670343f1f156b9
Source dataset
uspto-grants-2015_03
Patent number
US08975434B2

Reaction notes

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