Hydrochloric Acid → methyl (4E)-4-[(4-hydroxyphenyl)methoxyimino]-4-phenylbutanoate

HRID 1070069

반응식

HRID 1070069 반응식
COC[O:4][C:5]1[CH:13]=[CH:12][C:8]([CH2:9][O:10][NH2:11])=[CH:7][CH:6]=1.O=[C:15]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19].C([O-])(=O)C.[Na+].Cl>C(OCC)(=O)C.CCCCCC.CO.C(O)(=O)C>[OH:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:9][O:10]/[N:11]=[C:15](/[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)\[CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])=[CH:12][CH:13]=1

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 141190Benzenebutanoic acid, gamma-oxo-, methyl esterHCID 517045Sodium AcetateHCID 110522924-Methoxymethoxybenzyloxyamine

생성물 1

HCID 10946929methyl (4E)-4-[(4-hydroxyphenyl)methoxyimino]-4-phenylbutanoate수율 50%

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 887Methanol용매HCID 21226206Ethyl acetate hexane용매

실험 절차

A mixture of 4-methoxymethoxybenzyloxyamine (4.99 g), methyl 4-oxo-4-phenylbutyrate (5.71 g), acetic acid (5.10 ml), sodium acetate (4.87 g) and methanol (200 ml) was heated under reflux for 15 hours. The reaction mixture was cooled to room temperature, dilute hydrochloric acid was added to the residue and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The residue was dissolved in tetrahydrofuran (50 ml) and methanol (5 ml). To this solution was added 1N hydrochloric acid (10 ml) and heated under reflux for 3 hours. The reaction mixture was cooled to room temperature, water was added and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The residue was subjected to silica gel chromatography to obtain methyl E-4-(4-hydroxybenzyloxyimino)-4-phenylbutyrate (4.24 g, yield 50%) as a colorless oil from an ethyl acetate-hexane (2:5, v/v)-eluted fraction.

후처리

  1. temperaturewas heated
  2. temperatureunder reflux for 15 hours
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. dissolutionThe residue was dissolved in tetrahydrofuran (50 ml)
  8. additionTo this solution was added 1N hydrochloric acid (10 ml)
  9. temperatureheated
  10. temperatureunder reflux for 3 hours
  11. temperatureThe reaction mixture was cooled to room temperature
  12. additionwater was added
  13. extractionextracted with ethyl acetate
  14. washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
  15. dry with materialdried (MgSO4)
  16. concentrationconcentrated

출처 및 근거

ORD 기록
ord-2904a25793d140158972a0ed7e08db5c
출처 데이터셋
uspto-grants-2001_06
특허 번호
US06251926B1

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