Ammonium Chloride → 4-[Hydroxy(4-methoxyphenyl)methyl]benzonitrile

HRID 363049노트

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HRID 363049 반응식
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([C:7]([C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=2)=[O:8])=[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]([CH:7]([OH:8])[C:9]2[CH:10]=[CH:11][C:12]([C:13]#[N:14])=[CH:15][CH:16]=2)=[CH:17][CH:18]=1

참가 물질

5

반응물 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 108683214-(4-Methoxybenzoyl)benzonitrile

생성물 1

HCID 112419044-[Hydroxy(4-methoxyphenyl)methyl]benzonitrile

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a suspension of 4-(4-methoxybenzoyl)benzonitrile 26-1 (J. Med. Chem. 1991, 34, 2768-2778) (0.783 g, 3.3 mmol) in ethanol (35 ml) under nitrogen cooled in an ice-bath was added sodium borohydride (0.250 g, 6.6 mmol). The mixture was stirred 4 h with ice-bath cooling. To the resulting solution was added saturated ammonium chloride solution (35 ml). The mixture was partially evaporated under reduced pressure, and the resulting aqueous mixture was extracted with ethyl acetate (2×100 ml). The combined organic fractions were washed with brine (50 ml), dried (sodium sulfate), and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with ethyl acetate/hexane (1:6 increasing to 1:3), to give product 26-2 as an oil.

후처리

  1. temperaturecooled in an ice-bath
  2. temperaturecooling
  3. customThe mixture was partially evaporated under reduced pressure
  4. extractionthe resulting aqueous mixture was extracted with ethyl acetate (2×100 ml)
  5. washThe combined organic fractions were washed with brine (50 ml)
  6. dry with materialdried (sodium sulfate)
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by flash column chromatography on silica gel
  9. washeluting with ethyl acetate/hexane (1:6 increasing to 1:3)

출처 및 근거

ORD 기록
ord-6e1d016534724a41bb7df789afa80dfd
출처 데이터셋
uspto-grants-1999_02
특허 번호
US05872138

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