Dimethylformamide → HCID 54268796、化合物

HRID 1873148ノート

反応式

HRID 1873148 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:18]4[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][C:19]=4[S:20][C:16]=3[CH:15]=[C:14]3[C:9]=2[CH:10]=[CH:11][CH:12]=[CH:13]3)=[CH:4][CH:3]=1.Br[CH2:27][C:28]([O:30][CH3:31])=[O:29].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:31][O:30][C:28](=[O:29])[CH2:27][O:25][C:22]1[CH:23]=[CH:24][C:18]2[C:17]3[C:8]([C:5]4[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=4)=[C:9]4[C:14](=[CH:15][C:16]=3[S:20][C:19]=2[CH:21]=1)[CH:13]=[CH:12][CH:11]=[CH:10]4

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 1548123611-(4-Hydroxy-phenyl)-benzo[b]naphtho[2,3-d]thiophen-3-ol

生成物 1

HCID 54268796HCID 54268796、化合物収率 58.1%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

11-(4-Hydroxy-phenyl)-benzo[b]naphtho[2,3-d]thiophen-3-ol (1.36 g, 3.96 mmol), methyl bromoacetate (0.38 mL, 4.01 mmol), potassium carbonate (0.548 g, 3.97 mmol) and N,N-dimethylformamide (21 mL) were combined and stirred at ambient temperatures for 2.5 h. The reaction mixture was added to water and extracted with ethyl acetate and THF. Silica gel was added to the organic phase and the solvent was removed. The adsorbate was flash chromatographed (eluent:gradient dichloromethane to 98:2 dichloromethane:acetonitrile) to provide the title compound as a white solid (0.953 g, 58%): mp: 229-231° C: NMR (DMSO-d6); δ9.78 (s, 1 H), 8.51 (s, 1 H), 8.00 (d, J=8 Hz, 1 H), 7.56-7.39 (m, 4 H), 7.18 (d, J=9 Hz, 2 H), 7.05 (d, J=9 Hz, 2 H), 6.79 (dd, J=9, 2 Hz, 1 H), 6.66 (d, J=9 Hz, 1 H), 4.86 (s, 2 H), 3.68 (s, 3 H); MS (EI): 414 (100%, M+); Anal. Calc. for C25 H18O4S: C, 72.45, H, 4.38, N, 0.00. Found: C, 71.78, H, 4.41, N, 0.13.

後処理

  1. extractionextracted with ethyl acetate and THF
  2. additionSilica gel was added to the organic phase
  3. customthe solvent was removed
  4. customchromatographed (eluent:gradient dichloromethane to 98:2 dichloromethane:acetonitrile)

出典と根拠

ORDレコード
ord-543dc78195804bfdbf34a1d6469d4e36
出典データセット
uspto-grants-2000_08
特許番号
US06110962

反応ノート

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