Hydrochloric Acid → 2-(6-Chloropyridin-3-yl)ethan-1-ol

HRID 2400333Notes

Reaction equation

HRID 2400333 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9](O)=[O:10])=[CH:4][CH:3]=1.B.Cl.C(=O)(O)[O-].[Na+]>C1COCC1>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 516892Sodium BicarbonateHCID 140715712-(6-Chloropyridin-3-yl)acetic acid

Product 1

HCID 140715722-(6-Chloropyridin-3-yl)ethan-1-olYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To solid (6-chloro-pyridin-3-yl)-acetic acid (172 mg, 1 mmol) was added borane in THF (1M, 5 ml) and the reaction was stirred at room temperature. After 2 hours, the reaction was heated to 50 degC for 90 minutes. Aqueous hydrochloric acid (2N, 8 ml) was added to the reaction and it was allowed to cool to room temperature. After 10 minutes the reaction was basified with saturated aqueous sodium bicarbonate and extracted into ethyl acetate. The organic liquors were washed with water (×2) and brine, dried (MgSO4) and concentrated to furnish the crude product as a yellow oil (126 mg). This material was used as such in the coupling reaction. MS: [M+H]+158.

Workup

  1. temperaturethe reaction was heated to 50 degC for 90 minutes
  2. temperatureto cool to room temperature
  3. extractionextracted into ethyl acetate
  4. washThe organic liquors were washed with water (×2) and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a7af09d1d98e49b48ce8971dc0cc85f2
Source dataset
uspto-grants-2014_08
Patent number
US08796244B2

Reaction notes

Loading…