Ethanol → Ethyl 2-hydroxy-3-(4-methoxy-2-nitrophenoxy)-3-phenylpropanoate

HRID 2267631

反応式

HRID 2267631 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[C:5]([N+:10]([O-:12])=[O:11])[CH:4]=1.[C:13]1([CH:19]2[O:21][CH:20]2[C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(O)C.[H-].[Na+]>CO.ClCCl.ClCCl>[OH:21][CH:20]([CH:19]([O:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][C:5]=1[N+:10]([O-:12])=[O:11])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[C:22]([O:24][CH2:25][CH3:26])=[O:23]

参加物

7

反応物 4

HCID 702EthanolHCID 8469Ethyl 3-phenylglycidateHCID 15285Phenol, 4-methoxy-2-nitro-HCID 24758Sodium hydride

生成物 1

HCID 69706358Ethyl 2-hydroxy-3-(4-methoxy-2-nitrophenoxy)-3-phenylpropanoate

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 21226129Dichloromethane methanol溶媒

実験手順

To a stirred mixture of 4-methoxy-2-nitrophenol (11.87 g, 70 mmol), ethyl 3-phenyloxirane-2-carboxylate (10.39 g, 54 mmol) and ethanol (175 mL) was added portionwise 60% sodium hydride (0.65 g, 16 mmol) and the red mixture stirred at reflux for 9 days. The solvent was removed in vacuo, the residue dissolved in ethyl acetate and extracted three times with 10% aqueous potassium carbonate. The organic layer was washed with water and brine, dried (MgSO4), filtered and the solvent stripped in-vacuo to yield an oil. Column chromatography (dichloromethane then 5% methanol/dichloromethane) afforded (9.5 g, 49%) of slightly impure title compound that was used in the next step without further purification. 1H NMR (300 MHz, CDCl3) δ1.21 (t, 3H) 3.25 (d, 1H, J=7.5 Hz) 3.77 (s, 3H), 4.20 (q, 2H) 4.67 (q, 1H, J=3.5, 7.5 Hz), 5.51 (d, 1H, J=3.5 Hz), 6.82 (d, 1H, J=9.2 Hz), 6.92 (dd, 1H, J=9.2, 3.0 Hz), 7.3-7.4 (m, 6H). HPLC (Method A): 3.24 min.

後処理

  1. temperatureat reflux for 9 days
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue dissolved in ethyl acetate
  4. extractionextracted three times with 10% aqueous potassium carbonate
  5. washThe organic layer was washed with water and brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customto yield an oil

出典と根拠

ORDレコード
ord-814d4790c5b148db920a34d58a6f34e3
出典データセット
uspto-grants-2010_12
特許番号
US07858776B2

関連ノート

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