Ethyl 2-oxocyclopentanecarboxylate → Ethyl 2-hydroxycyclopentanecarboxylate

HRID 851507Notes

Reaction equation

HRID 851507 reaction equation
[BH4-].[Na+].[CH2:3]([O:5][C:6]([CH:8]1[CH2:12][CH2:11][CH2:10][C:9]1=[O:13])=[O:7])[CH3:4]>CO>[CH2:3]([O:5][C:6]([CH:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[OH:13])=[O:7])[CH3:4]

Participants

4

Reactant 2

HCID 69136Ethyl 2-oxocyclopentanecarboxylateHCID 4311764Sodium borohydride

Product 1

HCID 275611Ethyl 2-hydroxycyclopentanecarboxylateYield 69.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

1st method: 10 g of sodium borohydride are added to a solution of 62.4 g (0.4 mole) of 2-oxo-cyclopentylcarboxylic acid ethyl ester in 200 ml of methanol cooled to 0° C. When the reaction, which is followed by thin layer chromatography, is completed, the reaction mixture is poured with caution into an aqueous solution saturated with NaH2PO4. By extracting with ethyl ether and subsequently evaporating off the solvent, a residue is obtained which is purified by under vacuum distillation yielding 44 g of 2-hydroxy-cyclopentylcarboxylic acid ethyl ester (b.p. 87° C./0.3 mmHg).

Workup

  1. customWhen the reaction, which
  2. extractionBy extracting with ethyl ether
  3. customsubsequently evaporating off the solvent
  4. customa residue is obtained which
  5. distillationis purified by under vacuum distillation

Sources & evidence

ORD record
ord-5780be3a1d174ff3a1060830fef272d9
Source dataset
uspto-grants-1983_05
Patent number
US04385062

Reaction notes

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