Ethylene Glycol → 4-(3-Iodophenyl)morpholine

HRID 600998ノート

反応式

HRID 600998 の反応式
I[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([I:8])[CH:3]=1.[NH:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C(O)CO>C(O)(C)C.[Cu]I>[I:8][C:4]1[CH:3]=[C:2]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH:7]=[CH:6][CH:5]=1

参加物

7

反応物 4

HCID 174Ethylene GlycolHCID 8083MorpholineHCID 12270Benzene, 1,3-diiodo-HCID 62657Potassium Phosphate, Tribasic

生成物 1

HCID 545364344-(3-Iodophenyl)morpholine収率 41%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 3776Isopropanol溶媒

反応条件

温度
80 °C

実験手順

To a solution of 1,3-diiodobenzene (5.05 g, 15.3 mmol) in isopropanol (16 mL) under nitrogen was added morpholine (1.33 g, 1.33 mL, 15.3 mmol), potassium phosphate (6.50 g, 30.6 mmol), ethylene glycol (1.90 g, 1.70 mL, 30.6 mmol) and copper (I) iodide (146 mg, 0.765 mmol). The mixture was heated at 80° C. for 15 h, and then cooled to room temperature. The solids were removed by filtration and the solution was concentrated. The residue was purified by silica gel column chromatograghy eluted with EtOAc:hexanes (5 to 25% EtOAc) to give 4-(3-iodo-phenyl)-morpholine (1.81 g, 41%) as a colorless oil. MS (ES+): m/z=290.0; 1H NMR (CDCl3, 500 MHz): δ 3.15 (t, 4H), 3.85 (t, 4H), 6.87 (dd, 1H), 6.96-7.00 (m, 1H), 7.20 (d, 1H), 7.22-7.25 (m, 1H).

後処理

  1. temperaturecooled to room temperature
  2. customThe solids were removed by filtration
  3. concentrationthe solution was concentrated
  4. customThe residue was purified by silica gel column chromatograghy
  5. washeluted with EtOAc

出典と根拠

ORDレコード
ord-4fcfbfd189614470b9d6d45029dd6011
出典データセット
uspto-grants-2011_03
特許番号
US07902239B2

反応ノート

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