Sodium borohydride → 1,4-Bis(6-chloropyridin-3-yl)butane-1,4-diol

HRID 1471057Notes

Reaction equation

HRID 1471057 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8](=[O:20])[CH2:9][CH2:10][C:11]([C:13]2[CH:14]=[N:15][C:16]([Cl:19])=[CH:17][CH:18]=2)=[O:12])=[CH:4][CH:3]=1.[BH4-].[Na+]>C(O)C>[Cl:19][C:16]1[N:15]=[CH:14][C:13]([CH:11]([OH:12])[CH2:10][CH2:9][CH:8]([C:5]2[CH:6]=[N:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[OH:20])=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 596170251,4-Bis(6-chloropyridin-3-yl)butane-1,4-dione

Product 1

HCID 596171711,4-Bis(6-chloropyridin-3-yl)butane-1,4-diolYield 89.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The product from Example 207A (2.90 g, 9.38 mmol) and sodium borohydride (0.745 g, 19.70 mmol) were combined in ethanol (94 mL) at 0° C. The mixture was warmed to room temperature and stirred for 6 hours. The solvent was evaporated and the residue was partitioned between ethyl acetate and 1M HCl. The organic layer was washed with water, brine, dried with sodium sulfate, filtered and evaporated to give the title compound (2.62 g, 89%).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was partitioned between ethyl acetate and 1M HCl
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-5ebc77ca5fe24590a74fd3459e59a848
Source dataset
uspto-grants-2015_04
Patent number
US09006387B2

Reaction notes

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