Sodium borohydride → HCID 90022458, compound

HRID 1772873Notes

Reaction equation

HRID 1772873 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:11]=[C:10]([CH3:12])[CH:9]=[C:8]([F:13])[C:5]=1[CH:6]=[O:7]>CO.CCCCC>[Cl:3][C:4]1[CH:11]=[C:10]([CH3:12])[CH:9]=[C:8]([F:13])[C:5]=1[CH2:6][OH:7]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 90021510HCID 90021510, compound

Product 1

HCID 90022458HCID 90022458, compoundYield 76.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8003PentaneSolvent

Procedure

Sodium borohydride (1.42 g, 37.5 mmol) was added in portions to an ice-cooled solution of 2-chloro-6-fluoro-4-methylbenzaldehyde (6.25 g, 38.2 mmol) in methanol (56 mL); once addition was complete the reaction was allowed to warm rt with stirring over 1 h and then concentrated in vacuo. The residue was partitioned between ether and saturated aqueous sodium bicarbonate solution. The layers were separated and the aqueous re-extracted with ether. The organic layers were combined, washed with H2O, dried with MgSO4 and concentrated in vacuo to yield the crude product as an oil. This oil was diluted with pentane, cooled and stirred which resulted in a white solid. Filtration and drying in vacuo yielded the title compound (5.10 g, 29.2 mmol).

Workup

  1. additiononce addition
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between ether and saturated aqueous sodium bicarbonate solution
  4. customThe layers were separated
  5. extractionthe aqueous re-extracted with ether
  6. washwashed with H2O
  7. dry with materialdried with MgSO4
  8. concentrationconcentrated in vacuo
  9. customto yield the crude product as an oil
  10. temperaturecooled
  11. stirringstirred which
  12. customresulted in a white solid
  13. filtrationFiltration
  14. customdrying in vacuo

Sources & evidence

ORD record
ord-911f092685e64752a08d8ca6045a0517
Source dataset
uspto-grants-2016_02
Patent number
US09249160B2

Reaction notes

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