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

HRID 1534225ノート

反応式

HRID 1534225 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5365f9eb1fe64ba7ad2a61f23161ebb2
出典データセット
uspto-grants-1992_02
特許番号
US05087638

反応ノート

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