Hydrochloric Acid → 1-Ethoxy-3-(3'-ethoxy-4'-methoxyphenyl)-3-phthalimidopropane

HRID 1941251ノート

反応式

HRID 1941251 の反応式
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:12]([N:16]2[C:20](=[O:21])[C:19]3=[CH:22][CH:23]=[CH:24][CH:25]=[C:18]3[C:17]2=[O:26])[CH2:13][CH2:14][OH:15])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH3:2].[CH2:27](Br)[CH3:28].[H-].[Na+].Cl>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1.[NH4+].[Cl-]>[CH2:27]([O:15][CH2:14][CH2:13][CH:12]([C:6]1[CH:7]=[CH:8][C:9]([O:10][CH3:11])=[C:4]([O:3][CH2:1][CH3:2])[CH:5]=1)[N:16]1[C:20](=[O:21])[C:19]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:18]2[C:17]1=[O:26])[CH3:28]

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 6332Ethyl BromideHCID 24758Sodium hydrideHCID 214605203-(3'-Ethoxy-4'-methoxyphenyl)-3-phthalimido-1-propanol

生成物 1

HCID 214605291-Ethoxy-3-(3'-ethoxy-4'-methoxyphenyl)-3-phthalimidopropane収率 74%

試薬・触媒・溶媒 3

HCID 25517Ammonium Chloride触媒HCID 67553Tetrabutylammonium Iodide触媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of 3-(3'-ethoxy-4'-methoxyphenyl)-3-phthalimido-1-propanol (1 gram, 2.82 mmol), ethyl bromide (0.42 mL, 5.63 mmol), and tetrabutyl ammonium iodide (200 mg, 0.54 mmol) in THF (10 mL) at room temperature, was added NaH (270 mg, 60%, 6.75 mmol). The mixture was stirred at room temperature for 45 minutes, and then was heated to reflux for 4 h. To the mixture was added a few drops of NH4Cl, then HCl (1N, 25 mL). The organic layer was separated. The aqueous layer was extracted with ethyl acetate (3×25 mL). The combined organic layers were washed with brine (25 mL), and dried over magnesium sulfate. Removal of solvent and chromatography (silica gel 100 grams, 1:5 EtOAc:hexane) gave 1-ethoxy-3-(3'-ethoxy-4'-methoxyphenyl)-3-phthalimidopropane as an oil, (800 mg, 74% yield): 1H NMR (CDCl3)δ1.06 (t, J=7Hz, 3H, CH3), 1.46 (t, J=7 Hz, 3H, CH3), 2.46-2.58 (m, 1H, CHH), 2.75-2.95 (m, 1H, CHH), 3.37 (q, J=7 Hz, 2H, CH2), 3.44 (q, J=7 Hz, 2H, CH2), 3.85 (s, 3H, CH3), 4.12 (q, J=7 Hz, 2H, CH2), 5.49 (dd, J=6.4, 9.5 Hz, 1H, NCH), 6.81 (d, J=8.2 Hz, 1H, Ar), 7.10-7.48 (m, 2H, Ar), 7.68-7.72 (m, 2H, Ar), 7.77-7.83 (m, 2H, Ar); 13C NMR (CDCl3)δ14.73, 14.98, 31.31, 52.24, 55.89, 64.30, 66.33, 67.73, 111.11, 112.99, 120.61, 123.11, 132.00, 132.09, 133.80, 148.11, 148.84, 168.44; Anal Calcd for C22H25NO5 : C, 68.91; H, 6.57; N, 3.65. Found: C, 68.77; H, 6.47; N, 3.57.

後処理

  1. temperaturewas heated
  2. temperatureto reflux for 4 h
  3. customThe organic layer was separated
  4. extractionThe aqueous layer was extracted with ethyl acetate (3×25 mL)
  5. washThe combined organic layers were washed with brine (25 mL)
  6. dry with materialdried over magnesium sulfate
  7. customRemoval of solvent and chromatography (silica gel 100 grams, 1:5 EtOAc:hexane)

出典と根拠

ORDレコード
ord-7a91aeec5456493e9470e3895f677c03
出典データセット
uspto-grants-1997_12
特許番号
US05703098

反応ノート

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