4-Chloro-2-nitrophenol → Ethyl 2-hydroxy-3-(4-chloro-2-nitrophenoxy)-3-phenylpropanoate

HRID 2267616

反応式

HRID 2267616 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[C:12]1([CH:18]2[O:20][CH:19]2[C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[H-].[Na+]>C(O)C.C(Cl)(Cl)Cl>[OH:20][CH:19]([CH:18]([O:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=1[N+:9]([O-:11])=[O:10])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:21]([O:23][CH2:24][CH3:25])=[O:22]

参加物

6

反応物 3

HCID 69804-Chloro-2-nitrophenolHCID 8469Ethyl 3-phenylglycidateHCID 24758Sodium hydride

生成物 1

HCID 69705338Ethyl 2-hydroxy-3-(4-chloro-2-nitrophenoxy)-3-phenylpropanoate収率 33%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 6212Chloroform溶媒

実験手順

To a stirred mixture of 4-chloro-2-nitrophenol (11.68 g, 67.32 mmol), ethyl 3-phenyloxirane-2-carboxylate (9.61 g, 50.00 mmol) in ethanol (200 mL) was added portionwise 60% sodium hydride (738 mg, 20.00 mmol) and the red mixture stirred at reflux for 3 days. The solvent was removed in vacuo. The residue was dissolved in chloroform and extracted three times with 10% aqueous potassium carbonate. The organic layer was washed with water and brine, dried, filtered and evaporated to afford a brown residue. The residue was dissolved in a minimal volume of chloroform and precipitated by adding diethyl ether to afford the title compound (5.970 g, 33%) as an off-white solid. 1H NMR (300 MHz, DMSO-d6) δ1.16 (t, 3H, J=7.0 Hz), 4.09 (q, 2H, J=7.0 Hz), 4.29 (t, 1H, J=7.0 Hz), 5.63 (d, 1H, J=7.0 Hz), 6.09 (d, 1H, J=7.0 Hz), 7.19-7.60 (m, 7H), 7.97 (d, 1H, J=2.6 Hz). MS APCI, m/z=388 (M+Na). LC/MS: 2.78 min.

後処理

  1. temperatureat reflux for 3 days
  2. customThe solvent was removed in vacuo
  3. dissolutionThe residue was dissolved in chloroform
  4. extractionextracted three times with 10% aqueous potassium carbonate
  5. washThe organic layer was washed with water and brine
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. customto afford a brown residue
  10. customprecipitated
  11. additionby adding diethyl ether

出典と根拠

ORDレコード
ord-d26b55bec9964582bb5f7918e42c1d06
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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