Sodium borohydride → HCID 66841548, compound

HRID 2267845Notes

Reaction equation

HRID 2267845 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[C:9]([CH:12]=[O:13])=[CH:10][O:11][C:7]=2[CH:6]=[CH:5][CH:4]=1.[BH4-].[Na+]>CO>[CH3:1][O:2][C:3]1[C:8]2[C:9]([CH2:12][OH:13])=[CH:10][O:11][C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 82410987HCID 82410987, compound

Product 1

HCID 66841548HCID 66841548, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The aldehyde 123 from above (4.34 g, 24.63 mmol) is dissolved in 10 ml of methanol and cooled in an ice-bath. Solid sodium borohydride (4.9 g, 123.2 mmol) is added in portions and the mixture is stirred for 2 hours. It is then poured onto ice-cold HCl, extracted three times with DCM, dried and evaporated. The crude material is purified by chromatography on silicagel using hexane and EtOAc (from 20% to 50%).

Workup

  1. temperaturecooled in an ice-bath
  2. additionIt is then poured onto ice-cold HCl
  3. extractionextracted three times with DCM
  4. customdried
  5. customevaporated
  6. customThe crude material is purified by chromatography on silicagel

Sources & evidence

ORD record
ord-42d142cc0721406b843495d4178d2474
Source dataset
uspto-grants-2010_12
Patent number
US07858781B2

Reaction notes

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