Triethylamine → (E)-N-methoxy-4-(4-methoxyphenyl)-N-methylbut-3-enamide

HRID 1909535ノート

反応式

HRID 1909535 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[CH2:11][C:12]([OH:14])=O)=[CH:5][CH:4]=1.F[B-](F)(F)F.[N:20]1([O:29][C:30](N(C)C)=[N+](C)C)[C:24]2C=CC=CC=2N=N1.CCN(CC)CC>CN(C=O)C.O>[CH3:30][O:29][N:20]([CH3:24])[C:12](=[O:14])[CH2:11]/[CH:10]=[CH:9]/[C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 14713049(E)-4-(4-methoxyphenyl)but-3-enoic acid

生成物 1

HCID 22347543(E)-N-methoxy-4-(4-methoxyphenyl)-N-methylbut-3-enamide収率 30.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To the mixture of carboxylic acid (557) (5.7 g, 29.5 mmol) in DMF (150 mL) was added O-(Benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (9.5 g, 29.5 mol). After stifling for 5 minutes, N,O-dimethylhydroxylamine. HCl (2.9 g, 29.5 mmol) was added, followed by Et3N (8.2 mL, 58.9 mmol). The reaction mixture was stirred at room temperature for 3 hours, diluted with water and extracted with ethyl acetate. The organic phase was washed with water, brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (40% EtOAc in hexanes) to provide (E)-N-methoxy-4-(4-methoxyphenyl)-N-methylbut-3-enamide (558) (2.1 g, 29.6%) as a yellow solid.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with water, brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography on silica gel (40% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-b3f03fb2df44436097075e7406c2ce61
出典データセット
uspto-grants-2013_12
特許番号
US08598374B2

反応ノート

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