Ethyl Acetate → 907608-98-4

HRID 2410385Notes

Reaction equation

HRID 2410385 reaction equation
[CH:1]([C:3]1([C:8]([O:10][CH3:11])=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4]1)=[O:2].[BH4-].[Na+].C(OCC)(=O)C>C(O)C>[OH:2][CH2:1][C:3]1([C:8]([O:10][CH3:11])=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 10931680Methyl 1-formylcyclopentanecarboxylate

Product 1

HCID 57686715907608-98-4Yield 83.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of methyl 1-formylcyclopentanecarboxylate (954 mg, 6.11 mmol, Synthesis 1997, 32-34) in ethanol (10 mL) was added sodium tetrahydroborate (104 mg, 2.75 mmol) at ambient temperature. After being stirred for 30 min, the mixture was concentrated in vacuo to give an oil. The residual oil was dissolved with ethyl acetate, and the solution was washed with brine. The extract was dried over magnesium sulfate and concentrated in vacuo to afford 806 mg (83%) of the title compound as a colorless oil. The crude product was used in the next step without further purification.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customto give an oil
  3. washthe solution was washed with brine
  4. dry with materialThe extract was dried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3345c1c747db4480b6f816670a4b08f4
Source dataset
uspto-grants-2014_08
Patent number
US08816090B2

Reaction notes

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