Bismuth trichloride → Methyl 3-(4-((4-aminobenzyl)oxy)phenyl)propanoate

HRID 2422215Notes

Reaction equation

HRID 2422215 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][C:20]([O:22][CH3:23])=[O:21])=[CH:14][CH:13]=2)=[CH:6][CH:5]=1)([O-])=O.[Bi](Cl)(Cl)Cl.[BH4-].[Na+]>CO>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][C:20]([O:22][CH3:23])=[O:21])=[CH:14][CH:13]=2)=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 24591Bismuth trichlorideHCID 4311764Sodium borohydrideHCID 67145609Methyl 4-[(4-nitrophenyl)methoxy]benzenepropanoate

Product 1

HCID 23143251Methyl 3-(4-((4-aminobenzyl)oxy)phenyl)propanoateYield 27.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 4-[(4-nitrophenyl)methoxy]benzenepropanoate (0.55 g, 1.67 mmol) and bismuth (III) chloride (0.79 g, 2.5 mmol) in methanol (30 mL) was added sodium borohydride (0.51 g, 13 mmol), and the mixture was stirred at room temperature for 2 hrs. Insoluble material was filtered off, and the filtrate was concentrated. Water was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogencarbonate, dried and concentrated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=5:1) to give the title compound (0.13 g, yield 25%) as a powder.

Workup

  1. filtrationInsoluble material was filtered off
  2. concentrationthe filtrate was concentrated
  3. additionWater was added to the residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with saturated aqueous sodium hydrogencarbonate
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=5:1)

Sources & evidence

ORD record
ord-8768d27a3851444db178c9bad7f34756
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Reaction notes

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