Water → Ethyl 3-hydroxycyclopentanecarboxylate

HRID 340773Notes

Reaction equation

HRID 340773 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:10][CH2:9][C:8](=[O:11])[CH2:7]1)=[O:5])[CH3:2].[BH4-].[Na+].O>C1COCC1.CCOCC>[OH:11][CH:8]1[CH2:9][CH2:10][CH:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:7]1

Participants

6

Reactant 3

HCID 962WaterHCID 223136Ethyl 3-oxocyclopentanecarboxylateHCID 4311764Sodium borohydride

Product 1

HCID 53407781Ethyl 3-hydroxycyclopentanecarboxylate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of ethyl-3-oxo-cyclopentane-1-carboxylate (2.0 g) in THF (50 mL) was added NaBH4 (970 mg). The reaction mixture was maintained at 0° C. for 30 min, and then overnight at ambient temperature. The reaction was then treated with H2O and diluted with Et2O. The resulting layers were separated, and the aqueous layer was further extracted with Et2O. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated. The resulting crude product (a mixture of cis/trans isomers) was used in the next step without further purification.

Workup

  1. customovernight
  2. customat ambient temperature
  3. customThe resulting layers were separated
  4. extractionthe aqueous layer was further extracted with Et2O
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. additionThe resulting crude product (a mixture of cis/trans isomers)
  10. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-55821370c9df45f69e38da3985873785
Source dataset
uspto-grants-2014_11
Patent number
US08895596B2

Reaction notes

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