Hydrochloric Acid → (E)-N,2-bis(4-hydroxyphenyl)-3-phenylpent-2-enamide

HRID 884056Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 884056
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:30])/[C:10](/[C:20]2[CH:25]=[CH:24][C:23]([O:26]COC)=[CH:22][CH:21]=2)=[C:11](/[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)\[CH2:12][CH3:13])=[CH:4][CH:3]=1.Cl.O>CO.O1CCOCC1>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:30])/[C:10](/[C:20]2[CH:21]=[CH:22][C:23]([OH:26])=[CH:24][CH:25]=2)=[C:11](/[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)\[CH2:12][CH3:13])=[CH:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 68732343(E)-N-(4-hydroxyphenyl)-2-(4-(methoxymethoxy)phenyl)-3-phenylpent-2-enamide

Produkt 1

HCID 42603176(E)-N,2-bis(4-hydroxyphenyl)-3-phenylpent-2-enamideAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of 6a (45 mg, 0.112 mmol) in MeOH (1 ml) was added a solution of 4N HCl in dioxane (0.3 ml) under ice cooling, and the mixture was stirred at room temperature for 2 h. H2O was poured into the reaction mixture under ice cooling, and the whole was extracted with AcOEt. The organic layer was washed with brine, dried over Na2SO4, and then concentrated. The residue was crystallized with Et2O to give 7a (76%). 7a: colorless powder; 1H-NMR (CD3OD) δ 0.97 (3H, t, J=7.5 Hz), 2.64 (2H, q, J=7.5 Hz), 6.51 (2H, d, J=8.8 Hz), 6.76 (2H, d, J=8.8 Hz), 6.92 (2H, d, J=8.8 Hz), 7.12-7.25 (5H, m), 7.40 (2H, d, J=8.8 Hz). HRMS calcd for C23H22NO3: 360.1600. Found: 360.1605.

Aufarbeitung

  1. extractionthe whole was extracted with AcOEt
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was crystallized with Et2O

Quellen und Nachweise

ORD-Eintrag
ord-02f0ebc8d17a4d32bf800f77e64a17e5
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08236987B2

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