Formaldehyde → 1-(4-Chlorobenzyl)-3-hydroxymethyl-3-methyl-2-oxocyclopentanecarboxylic acid methyl ester

HRID 873509Notes

Reaction equation

HRID 873509 reaction equation
C=O.[C:3](=O)([O-])[O-:4].[K+].[K+].[CH3:9][O:10][C:11]([C:13]1([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)[CH2:17][CH2:16][CH:15]([CH3:18])[C:14]1=[O:19])=[O:12]>O>[CH3:9][O:10][C:11]([C:13]1([CH2:20][C:21]2[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][CH:26]=2)[CH2:17][CH2:16][C:15]([CH2:3][OH:4])([CH3:18])[C:14]1=[O:19])=[O:12]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 11430Potassium CarbonateHCID 11482916115851-54-2

Product 1

HCID 672540121-(4-Chlorobenzyl)-3-hydroxymethyl-3-methyl-2-oxocyclopentanecarboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 37% formaldehyde aqueous solution (0.90 ml) and potassium carbonate (2.00 mmol) were added to 1-(4-chlorobenzyl)-3-methyl-2-oxocyclopentanecarboxylic acid methyl ester (Compound VIII-1) (4.00 mmol), and the resultant mixture was stirred at room temperature for 4 hours. After the reaction, water was added to the resultant reaction solution, and the 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 a residue was purified with the use of a silica gel column. In this way, Compound VII-1 in the form of two isomers (isomer VII-1a and isomer VII-1b) was obtained. Note that Compound VIII-1 was synthesized in accordance with a method described in Patent Literature 1.

Workup

  1. additionwas added to the resultant
  2. customreaction solution
  3. extractionthe solution was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off
  7. customa residue was purified with the use of a silica gel column
  8. customIn this way, Compound VII-1 in the form of two isomers (isomer VII-1a and isomer VII-1b) was obtained
  9. customwas synthesized in accordance with a method

Sources & evidence

ORD record
ord-6141951a41ba40f2aeb549412c2eabb3
Source dataset
uspto-grants-2015_03
Patent number
US08975434B2

Reaction notes

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