Hydrochloric Acid → HCID 22846170, compound

HRID 1886490Notes

Reaction equation

HRID 1886490 reaction equation
[CH3:1][C@@H:2]1[CH2:6][C:5](=[O:7])[CH2:4][C@H:3]1[C:8]([O:10]C)=[O:9].[OH-].[Na+].Cl>CO>[CH3:1][C@@H:2]1[CH2:6][C:5](=[O:7])[CH2:4][C@H:3]1[C:8]([OH:10])=[O:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 13451548HCID 13451548, compound

Product 1

HCID 22846170HCID 22846170, compoundYield 48.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl trans-2-methyl-4-oxocyclopentanecarboxylate [K. Kojima et at., Chem. Pharm. Bull., 33, 2750 (1985)] (495 mg) was dissolved in methanol (3 ml), and a 1N aqueous solution of sodium hydroxide (3.5 ml) was added to the solution at 0° C. After the mixture was stirred at room temperature for 1 hour, it was acidified with dilute hydrochloric acid, followed by extraction with ether. The extract was concentrated to dryness and the residue was subjected to silica gel column chromatography with ethyl acetate-chloroform (1:1) as eluent, and the eluted fractions were combined and concentrated to dryness to afford the title compound (219 mg) as crystals.

Workup

  1. extractionfollowed by extraction with ether
  2. concentrationThe extract was concentrated to dryness
  3. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-9967c0f6a8c747eaa17da79bcf27e71b
Source dataset
uspto-grants-1992_09
Patent number
US05151497

Reaction notes

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