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

HRID 884056ノート

反応式

HRID 884056 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 312751,4-Dioxane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-02f0ebc8d17a4d32bf800f77e64a17e5
出典データセット
uspto-grants-2012_08
特許番号
US08236987B2

反応ノート

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