Ammonium Chloride → 2-(2,6-Dichloropyridin-3-yl)ethan-1-ol

HRID 595758Notes

Reaction equation

HRID 595758 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[C:9]([CH2:10][CH:11]=[O:12])=[CH:8][CH:7]=[C:6]([Cl:13])[N:5]=1.[NH4+].[Cl-]>C1COCC1.CO>[Cl:3][C:4]1[C:9]([CH2:10][CH2:11][OH:12])=[CH:8][CH:7]=[C:6]([Cl:13])[N:5]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 220381052-(2,6-Dichloropyridin-3-yl)acetaldehyde

Product 1

HCID 184274292-(2,6-Dichloropyridin-3-yl)ethan-1-olYield 99.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

NaBH4 (80 mg, 2.11 mmol) was added to a solution of 2-(2,6-dichloropyridin-3-yl)acetaldehyde (200 mg, 1.05 mmol) in THF (1 ml) and MeOH (1 ml) and stirred at RT for 1 hour. The resulting mixture was treated with NH4Cl and extracted with EtOAc. The organic layer was washed with brine, dried (Na2SO4), filtered and concentrated in vacuo to give the yellow oil 2-(2,6-dichloropyridin-3-yl)ethanol (200 mg, yield: 99%)

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-76541ea39a0743678bfaf8c535549ca3
Source dataset
uspto-grants-2016_01
Patent number
US09243002B2

Reaction notes

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