Sodium borohydride → HCID 19934850, compound

HRID 37242Notes

Reaction equation

HRID 37242 reaction equation
[CH3:1][C:2]1[CH:20]=[C:19]([CH:21]=[O:22])[CH:18]=[C:17]([CH3:23])[C:3]=1[O:4][CH:5]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=1)[C:6]([O:8][CH3:9])=[O:7].[BH4-].[Na+]>CO>[CH3:1][C:2]1[CH:20]=[C:19]([CH2:21][OH:22])[CH:18]=[C:17]([CH3:23])[C:3]=1[O:4][CH:5]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=1)[C:6]([O:8][CH3:9])=[O:7]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 18950590Methyl 2-(2,6-dimethyl-4-formylphenoxy)-2-(3-chlorophenyl)acetate

Product 1

HCID 19934850HCID 19934850, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a magnetically solution of 1.26 g (3.8 mmol) of the product of Step A in 8 mL of methanol was added 0.072 g (1.9 mmol) of sodium borohydride at 0° C. After stirring for 10 minutes, the reaction mixture was partitioned between EtOAc and water. The organic layer was separated, dried (MgSO4), filtered and evaporated. The residue was purified on a silica gel flash chromatography column eluted with 30% EtOAc-hexane. Combination of the purified fractions and drying in vacuo afforded 0.790 g (63%) of the title compound.

Workup

  1. customthe reaction mixture was partitioned between EtOAc and water
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified on a silica gel flash chromatography column
  7. washeluted with 30% EtOAc-hexane
  8. customCombination of the purified fractions and drying in vacuo

Sources & evidence

ORD record
ord-988715889dfc400e99eb91b4fb7373df
Source dataset
uspto-grants-1995_05
Patent number
US05420133

Reaction notes

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