Sodium borohydride → HCID 54290525, compound

HRID 2293589Notes

Reaction equation

HRID 2293589 reaction equation
[Si:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[C:11]([CH2:17][CH2:18][CH3:19])[CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[BH4-].[Na+]>C(O)C>[Si:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][OH:14])=[C:11]([CH2:17][CH2:18][CH3:19])[CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 214769234-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-2-propylbenzaldehyde

Product 1

HCID 54290525HCID 54290525, compoundYield 66.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 0.386 g (1.32 mmol) of the product of Step D dissolved in 4.0 mL of ethanol was added 0.025 g (0.66 mmol) of sodium borohydride and the reaction mixture was stirred at room temperature for 30 minutes. The excess reducing agent was then quenched with 10% aqueous NaHSO4 and the methanol was removed in vacuo. The residue was partitioned between EtOAc and water and extracted, the organic layer was separated, dried (MgSO4), filtered and evaporated. The residue was purified on a silica gel flash chromatography column eluted with 15% EtOAc-hexane. Evaporation of the purified fractions and solvent removal in vacuo afforded 0.246 g (63%) of the title compound.

Workup

  1. customwas then quenched with 10% aqueous NaHSO4
  2. customthe methanol was removed in vacuo
  3. customThe residue was partitioned between EtOAc and water
  4. extractionextracted
  5. customthe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified on a silica gel flash chromatography column
  10. washeluted with 15% EtOAc-hexane
  11. customEvaporation of the purified fractions and solvent removal in vacuo

Sources & evidence

ORD record
ord-ad2c9fb1d09441af9600294255985a59
Source dataset
uspto-grants-1997_11
Patent number
US05686478

Reaction notes

Loading…