Ammonium Chloride → 2-(p-Methoxybenzyl)-3,7-dimethyl-4-hydroxy-5-propylbenzofuran

HRID 1534225Notes

Reaction equation

HRID 1534225 reaction equation
[CH3:1][O:2][C:3]1[CH:27]=[CH:26][C:6]([CH2:7][C:8]2[O:9][C:10]3[C:17]([CH2:18]N(C)C)=[CH:16][C:15]([CH2:22][CH2:23][CH3:24])=[C:14]([OH:25])[C:11]=3[C:12]=2[CH3:13])=[CH:5][CH:4]=1.[BH4-].[Na+].[Cl-].[NH4+]>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][C:8]2[O:9][C:10]3[C:17]([CH3:18])=[CH:16][C:15]([CH2:22][CH2:23][CH3:24])=[C:14]([OH:25])[C:11]=3[C:12]=2[CH3:13])=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 145708982-(p-Methoxybenzyl)-3-methyl-4-hydroxy-5-propyl-7-dimethylaminomethylbenzofuran

Product 1

HCID 145708992-(p-Methoxybenzyl)-3,7-dimethyl-4-hydroxy-5-propylbenzofuranYield 91.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-(p-methoxybenzyl)-3-methyl-4-hydroxy-5-propyl-7-dimethylaminomethylbenzofuran (0.2 gm; 0.54 mmole) in ethanol (5 mL) was added sodium borohydride (0.2 gm, 5.45 mmoles) and the reaction mixture was refluxed for 10 minutes. The reaction mixture was cooled, poured in a saturated solution of ammonium chloride, and extracted with ether. The organic phase was washed with with brine, dried (Na2SO4), and concentrated in vacuo. The residue was chromatographed on silica gel using 20% ethylacetate in hexane as eluent to yield 160 mg (91%) of 2-(p-methoxybenzyl)-3,7-dimethyl-4-hydroxy-5-propylbenzofuran, mp. 102°-104° C.

Workup

  1. temperaturethe reaction mixture was refluxed for 10 minutes
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted with ether
  4. washThe organic phase was washed with with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed on silica gel using 20% ethylacetate in hexane as eluent

Sources & evidence

ORD record
ord-5365f9eb1fe64ba7ad2a61f23161ebb2
Source dataset
uspto-grants-1992_02
Patent number
US05087638

Reaction notes

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