Sodium borohydride → HCID 86686043, compound

HRID 239135Notes

Reaction equation

HRID 239135 reaction equation
[BH4-].[Na+].[CH2:3]([N+:10]1[CH:15]=[CH:14][C:13]([C:16]2[O:17][C:18]([CH3:21])=[CH:19][N:20]=2)=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C(O)C>[CH2:3]([N:10]1[CH2:11][CH:12]=[C:13]([C:16]2[O:17][C:18]([CH3:21])=[CH:19][N:20]=2)[CH2:14][CH2:15]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86686044HCID 86686044, compound

Product 1

HCID 86686043HCID 86686043, compoundYield 61.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

21.6 g sodium borohydride was added to 130 g 1-benzyl-4-(5-methyl-oxazol-2-yl)-pyridinium in 1.5 L ethanol at 0° C. under nitrogen. The reaction was stirred 30 min at 0° C. and 2 h at RT. The mixture was concentrated and treated with water and ethyl acetate. The organic layer was separated and washed with brine and evaporated. The residue was purified by chromatographie on silica to give 81.2 g of the desired product.

Workup

  1. concentrationThe mixture was concentrated
  2. additiontreated with water and ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with brine
  5. customevaporated
  6. customThe residue was purified by chromatographie on silica

Sources & evidence

ORD record
ord-936df5545d174ddaa9cc044533dd8285
Source dataset
uspto-grants-2014_02
Patent number
US08642774B2

Reaction notes

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