Sodium borohydride → HCID 59729434, compound

HRID 1669296Notes

Reaction equation

HRID 1669296 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH:9]=[O:10])=[CH:4][CH:3]=1.[BH4-].[Na+]>C(O)C>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH2:9][OH:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 59729415HCID 59729415, compound

Product 1

HCID 59729434HCID 59729434, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

2-(6-Chloro-pyridin-3-yl)-octanal (1.02 g, 4.26 mmol) is dissolved into denatured ethanol (20 mL) at room temperature then cooled to 0° C. in an ice bath. Sodium borohydride (0.162 g, 4.26 mmol) is then carefully added in small portions. The reaction is allowed to warm slowly to room temperature and is monitored by HPLC. Upon complete consumption of starting material, the reaction is carefully quenched with water and diluted with ethyl acetate. The ethanol is removed and the residue is extracted with ethyl acetate, washed, dried, and concentrated. The 2-(6-Chloro-pyridin-3-yl)-octan-1-ol (0.856 g, 3.55 mmol), 83%, is obtained in purified form after flash column chromatography.

Workup

  1. temperatureto warm slowly to room temperature
  2. customUpon complete consumption of starting material
  3. customthe reaction is carefully quenched with water
  4. additiondiluted with ethyl acetate
  5. customThe ethanol is removed
  6. extractionthe residue is extracted with ethyl acetate
  7. washwashed
  8. customdried
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-baa354baf8224db4a0412d04f9b0d649
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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