Sodium borohydride → HCID 69265731, compound

HRID 899242Notes

Reaction equation

HRID 899242 reaction equation
[Si:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[C:11]([Cl:17])[CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[BH4-].[Na+]>CO>[Si:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][OH:14])=[C:11]([Cl:17])[CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 589074694-[(Tert-butyldimethylsilyl)oxy]-2-chlorobenzaldehyde

Product 1

HCID 69265731HCID 69265731, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 4-{[tert-butyl(dimethyl)silyl]oxy}-2-chlorobenzaldehyde (WO 2003051797, 1.58 g, 5.83 mmol) in methanol (5 mL) was added sodium borohydride (264 mg, 7.00 mmol) at 0° C. The mixture was stirred at room temperature for 3 h, and quenched by addition of aqueous ammonium chloride. The mixture was extracted with ethyl acetate (200 mL), and the organic layer was washed with brine, dried over sodium sulfate, and evaporated. The residue was purified by column chromatography on silica gel (100 g) eluting with hexane/ethyl acetate (20/1 to 10/1) to afford 1.51 g (95%) of the title compound as a colorless oil:

Workup

  1. customquenched by addition of aqueous ammonium chloride
  2. extractionThe mixture was extracted with ethyl acetate (200 mL)
  3. washthe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customThe residue was purified by column chromatography on silica gel (100 g)
  7. washeluting with hexane/ethyl acetate (20/1 to 10/1)

Sources & evidence

ORD record
ord-3e24289a6cd743ada013ed6d19c19d44
Source dataset
uspto-grants-2008_04
Patent number
US07354925B2

Reaction notes

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