Sodium Bicarbonate → HCID 19798093, compound

HRID 1640876Notes

Reaction equation

HRID 1640876 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[N:9]=[CH:8][C:7]([C:10](=[O:12])[CH3:11])=[CH:6][CH:5]=1.C([O-])(O)=O.[Na+]>CO>[Cl:3][C:4]1[N:9]=[CH:8][C:7]([CH:10]([OH:12])[CH3:11])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 27796981-(6-Chloropyridin-3-yl)ethan-1-oneHCID 4311764Sodium borohydride

Product 1

HCID 19798093HCID 19798093, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add sodium tetrahydroborate (1.01 g, 26.35 mmol) slowly to a solution of 1-(6-chloro-pyridin-3-yl)-ethanone (10 g, 64.27 mmol) in methanol (100 mL). Stir at RT for 15 min. Pour the reaction mixture into a beaker containing saturated NaHCO3 (40 mL) and then extract between water (100 mL) and DCM (400 mL). Wash the organic layers with saturated aqueous sodium chloride, dry over sodium sulfate and concentrate. Purify by normal phase column chromatography (20% ethyl acetate in hexanes→70% ethyl acetate in hexanes) to afford the title compound (7 g, 69%). MS (ES) m/z 158 [M+1]+.

Workup

  1. additionPour the reaction mixture into a beaker
  2. extractionextract between water (100 mL) and DCM (400 mL)
  3. washWash the organic layers with saturated aqueous sodium chloride
  4. dry with materialdry over sodium sulfate
  5. concentrationconcentrate
  6. customPurify by normal phase column chromatography (20% ethyl acetate in hexanes→70% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-aab12226a61f46b988f160910018cc0d
Source dataset
uspto-grants-2012_02
Patent number
US08114872B2

Reaction notes

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