Sodium borohydride → HCID 23109584, compound

HRID 968977Notes

Reaction equation

HRID 968977 reaction equation
[C:1]([C:4]1[CH:22]=[CH:21][CH:20]=[CH:19][C:5]=1[O:6][C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][C:8]=1[O:17][CH3:18])(=[O:3])[CH3:2].[BH4-].[Na+]>CO>[OH:3][CH:1]([C:4]1[CH:22]=[CH:21][CH:20]=[CH:19][C:5]=1[O:6][C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][C:8]=1[O:17][CH3:18])[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 23109600HCID 23109600, compound

Product 1

HCID 23109584HCID 23109584, compoundYield 66.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 4-(2-acetylphenoxy)-3-methoxybenzoate (1.24 g) obtained in Step 1 was dissolved in methanol (20 ml), and after ice-cooling, sodium borohydride (312 mg) was added. The mixture was stirred for 2 hrs. The reaction mixture was concentrated under reduced pressure, and water was added. The mixture was extracted with ethyl acetate. The organic layer was washed successively with 5% aqueous citric acid solution and brine, and dried over sodium sulfate. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1) to give the title compound (834 mg).

Workup

  1. temperatureafter ice-cooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure, and water
  3. additionwas added
  4. extractionThe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed successively with 5% aqueous citric acid solution and brine
  6. dry with materialdried over sodium sulfate
  7. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-28eec05f3aff49799856427cc67da6aa
Source dataset
uspto-grants-2007_12
Patent number
US07304174B2

Reaction notes

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