Allyl bromide → HCID 22904998、化合物

HRID 865335ノート

反応式

HRID 865335 の反応式
[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]2[CH2:7][CH2:8][CH2:9][NH:10][C:11](=[O:12])[C:5]=2[CH:4]=1.[H-].[Na+].[CH2:17](Br)[CH:18]=[CH2:19]>CN(C)C=O.[Cl-].[Na+].O>[CH2:19]([N:10]1[CH2:9][CH2:8][CH2:7][C:6]2[CH:13]=[CH:14][C:3]([O:2][CH3:1])=[CH:4][C:5]=2[C:11]1=[O:12])[CH:18]=[CH2:17]

参加物

6

反応物 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 112755298-Methoxy-2,3,4,5-tetrahydro-benzo[c]azepin-1-one

生成物 1

HCID 22904998HCID 22904998、化合物収率 83%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

A solution of 8-methoxy-2,3,4,5-tetrahydro-1H-2-benzazepin-1-one (10.0 g, 0.052 mol) in N,N-dimethylformamide (30 mL) and allylbromide (23 mL, 0.260 mL) was treated with NaH (60% by wt. dispersion in oil, 2.50 g, 0.063 mol) and the resulting grey suspension stirred at room temperature under an atmosphere of argon. Gas evolution was noted. After 15 minutes, the solution was diluted with brine and partitioned between ethyl acetate and brine. The combined organic layers were concentrated in vacuo and purified by chromatography over silica gel eluting with a gradient of hexane to 1:1 ethyl acetate/hexane to yield 8 g (83%) of 2-allyl-8-methoxy-2,3,4,5-tetrahydro-1H-2-benzazepin-1-one as a colorless oil: 1H NMR(CDCl3) d7.23(m, 1H), 7.03(d, J=9 Hz, 1H), 6.90(dd, J=3, 9 Hz, 1H), 5.91(m, 1H), 5.23(m, 2H), 4.20(d, J=6 Hz, 2H), 3.82(s, 3H), 3.18(t, J=6 Hz, 2H), 2.72(t, J=6 Hz, 2H), 1.96(pentet, J=6 Hz, 2H); 13C NMR(CDCl3) d170.59(CO), 158.42(NCO), 136.88, 133.81, 129.43, 129.35, 129.33, 117.56, 117.54, 112.98, 55.26, 49.43, 45.37, 29.57, 29.22; MS(FAB)m/z=232.1(MH+).

後処理

  1. custompartitioned between ethyl acetate and brine
  2. concentrationThe combined organic layers were concentrated in vacuo
  3. custompurified by chromatography over silica gel eluting with a gradient of hexane to 1:1 ethyl acetate/hexane

出典と根拠

ORDレコード
ord-e6f7f3710ee24f37b0079fd5a8625732
出典データセット
uspto-grants-1996_10
特許番号
US05565449

反応ノート

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