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

HRID 884056노트

반응식

HRID 884056 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 312751,4-Dioxane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-02f0ebc8d17a4d32bf800f77e64a17e5
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08236987B2

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