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

HRID 1534225노트

반응식

HRID 1534225 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5365f9eb1fe64ba7ad2a61f23161ebb2
출처 데이터셋
uspto-grants-1992_02
특허 번호
US05087638

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