Sodium borohydride → HCID 86677774, compound

HRID 1499850Notes

Reaction equation

HRID 1499850 reaction equation
[BH4-].[Na+].[Br:3][C:4]1[C:5]([O:15][CH2:16][CH3:17])=[C:6]([C:12](=[O:14])[CH3:13])[CH:7]=[C:8]([Cl:11])[C:9]=1[CH3:10]>CO>[Br:3][C:4]1[C:5]([O:15][CH2:16][CH3:17])=[C:6]([CH:12]([OH:14])[CH3:13])[CH:7]=[C:8]([Cl:11])[C:9]=1[CH3:10]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86677773HCID 86677773, compound

Product 1

HCID 86677774HCID 86677774, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium tetrahydroborate (0.31 g, 8.1 mmol) was added to a mixture of 1-(3-bromo-5-chloro-2-ethoxy-4-methylphenyl)ethanone (1.5 g, 5.4 mmol) in methanol (25 mL) at 0° C. and the resultant reaction mixture was stirred at room temperature for 1 hour. The solvent was removed and the resulting residue was diluted with ethyl acetate, washed with sat. NaHCO3, water, brine, then dried over Na2SO4, filtered and concentrated. The crude product was purified by silica gel chromatography, eluting with 0 to 30% EtOAc in hexanes (0.30 g, 90%).

Workup

  1. customthe resultant reaction mixture
  2. customThe solvent was removed
  3. additionthe resulting residue was diluted with ethyl acetate
  4. washwashed with sat. NaHCO3, water, brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by silica gel chromatography
  9. washeluting with 0 to 30% EtOAc in hexanes (0.30 g, 90%)

Sources & evidence

ORD record
ord-7480c7e92b704cdba14889a3d4462790
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

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