Ethyl bromoacetate → HCID 69411210、化合物

HRID 1373879ノート

反応式

HRID 1373879 の反応式
[S:1]1[C:5]([C:6]2[CH:7]=[C:8]3[C:13](=[CH:14][CH:15]=2)[C:12]([Cl:16])=[C:11]([OH:17])[CH:10]=[CH:9]3)=[CH:4][C:3]2[CH:18]=[CH:19][CH:20]=[CH:21][C:2]1=2.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31]>CC(C)=O>[CH2:33]([O:32][C:30](=[O:31])[CH2:29][O:17][C:11]1[CH:10]=[CH:9][C:8]2[C:13](=[CH:14][CH:15]=[C:6]([C:5]3[S:1][C:2]4[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=4[CH:4]=3)[CH:7]=2)[C:12]=1[Cl:16])[CH3:34]

参加物

5

反応物 3

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 21075903HCID 21075903、化合物

生成物 1

HCID 69411210HCID 69411210、化合物収率 67%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

A mixture of 6-benzo[b]thiophen-2-yl-1-chloro-naphthalen-2-ol (3.19 g, 10.2 mmol) and cesium carbonate (6.8 g, 21 mmol) in acetone (100 mL) was stirred at ambient temperature for one hour and 15 minutes. Ethyl bromoacetate (1.4 mL, 12 mmol) was added, and the reaction mixture was stirred for 3.5 hours at ambient temperature. The insoluble solids were then filtered, and the filtrate was solvent evaporated. The residue was dissolved in hot chloroform and washed with water and brine. It was dried with anhydrous magnesium sulfate, filtered and solvent evaporated. The residue was then stirred in hexane for about ten minutes and filtered and rinsed with hexane. Drying at 65° C. in vacuo for two hours yielded (6-benzo[b]thiophen-2-yl-1-chloro-naphthalen-2-yloxy)-acetic acid ethyl ester as a light yellow solid (2.7 g, 67%): MP: 187–8° C.; Mass spectrum (+ES, [M+H]+) m/z 397/399. 1HNMR (500 MHz, DMSO-d6): δ8.34 (d, 1H, J=1.68 Hz), 8.21 (d, 1H, J=8.85 Hz), 8.13 (dd, 1H, J=8.93 and 1.76 Hz), 8.01–8.07 (m, 3H), 7.89–7.90 (m, 1H), 7.52 (d, 1H, J=9.15 Hz), 7.37–7.44 (m, 2H), 5.11 (s, 2H), 4.20 (q, 2H, J=7.12 Hz), 1.23 ppm (t, 3H, J=7.10 Hz). Elemental Analysis for C22H17ClO3S: Calcd: C, 66.58; H, 4.32; N, 0.00; Found: C, 66.43; H, 4.27; N, 0.00.

後処理

  1. stirringthe reaction mixture was stirred for 3.5 hours at ambient temperature
  2. filtrationThe insoluble solids were then filtered
  3. customevaporated
  4. dissolutionThe residue was dissolved in hot chloroform
  5. washwashed with water and brine
  6. dry with materialIt was dried with anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customsolvent evaporated
  9. stirringThe residue was then stirred in hexane for about ten minutes
  10. filtrationfiltered
  11. washrinsed with hexane
  12. customDrying at 65° C. in vacuo for two hours

出典と根拠

ORDレコード
ord-fc0831ce40764f57b36116c8d313512e
出典データセット
uspto-grants-2007_01
特許番号
US07163954B2

反応ノート

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