Sodium borohydride → 2-Cyano-3-(3-pyridyl)propionaldehyde dimethylacetal

HRID 496825Notes

Reaction equation

HRID 496825 reaction equation
[CH3:1][O:2][CH:3]([O:14][CH3:15])[C:4](=[CH:7][C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1)[C:5]#[N:6].[BH4-].[Na+]>C(O)C>[CH3:15][O:14][CH:3]([O:2][CH3:1])[CH:4]([C:5]#[N:6])[CH2:7][C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 541103342-Dimethoxymethyl-3-(3-pyridyl)acrylonitrile

Product 1

HCID 223233282-Cyano-3-(3-pyridyl)propionaldehyde dimethylacetalYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-dimethoxymethyl-3-(3-pyridyl)acrylonitrile, obtained according to the process of Example 4 (20.4 6, 0.1 mol), absolute ethanol (200 mL) and sodium borohydride (1.6 g, 0.042 mol) was stirred at room temperature overnight. Most of the ethanol was evaporated in vacuo and the residue was partitioned between ethyl acetate (200 mL) and water (200 mL). The organic layer was separated, washed with saturated brine, dried (Na2SO4) and evaporated in vacuo. The residual oil was distilled in vacuo to give a pale-yellow oil (19.1 g, 93%), bp. 130-140° C. (0.2 mm Hg).

Workup

  1. customobtained
  2. customMost of the ethanol was evaporated in vacuo
  3. customthe residue was partitioned between ethyl acetate (200 mL) and water (200 mL)
  4. customThe organic layer was separated
  5. washwashed with saturated brine
  6. dry with materialdried (Na2SO4)
  7. customevaporated in vacuo
  8. distillationThe residual oil was distilled in vacuo

Sources & evidence

ORD record
ord-deb5d523648342448ef683815bd25277
Source dataset
uspto-grants-2005_09
Patent number
US06946554B2

Reaction notes

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