Pyridine → 2-Ethylcarbonate Ethylmaleimide

HRID 23966ノート

反応式

HRID 23966 の反応式
[OH:1][CH2:2][CH2:3][C:4]1[C:5]([NH:7][C:8](=[O:10])[CH:9]=1)=[O:6].N1C=CC=CC=1.Cl[C:18]([O:20][CH2:21][CH3:22])=[O:19]>C1COCC1>[CH2:3]([C:4]1[C:5]([NH:7][C:8](=[O:10])[CH:9]=1)=[O:6])[CH3:2].[CH3:22][CH2:21][O:20][C:18](=[O:1])[OH:19]

参加物

5

反応物 3

HCID 1049PyridineHCID 10928Ethyl chloroformateHCID 22337974Hydroxy ethylmaleimide

生成物 1

HCID 685376102-Ethylcarbonate Ethylmaleimide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Hydroxy ethylmaleimide (29.87 g, 0.212 moles) and pyridine (16.7 g, 0.212 moles) were dissolved in THF (170 mL) and the solution was stirred at room temperature. Ethyl chloroformate (22.97 g, 0.212 moles) was added dropwise and stirred for 90 minutes. The pyridine salt was filtered off and the solution was combined with 200 mL of a 1N HCl solution. The product was extracted with methylene chloride and washed with a 1N HCl solution followed by water and then dried over magnesium sulfate. The red solution was concentrated and the red crystals purified by sublimation yielding white crystals, m.p. 52° C. (34.76 g, 77.04%). 1H-NMR (CDCl3), δ, ppm): 1.26-1.34 (3H, —CH3, t), 3.81-3.87 (2H —NCH2—, t), 4.14-4.25 (2H, δ-CH2OC═O, q), 4.25-4.30 (2H, β-CH2O—, t), 6.74 (2H, —CH═CH—, s). 13C-NMR (CDCl3, δ, ppm): 14.2 (1C, —CH3), 36.8 (1C, —NCH2—), 64.3 (1C, δ-CH2O), 64.5 (1C, β-CH2—), 134.4 (2C, —CH═CH—), 154.9 (1C, O(C═O)O), 170.4 (2C, —C═O).

後処理

  1. stirringstirred for 90 minutes
  2. filtrationThe pyridine salt was filtered off
  3. extractionThe product was extracted with methylene chloride
  4. washwashed with a 1N HCl solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationThe red solution was concentrated
  7. customthe red crystals purified by sublimation
  8. customyielding white crystals, m.p. 52° C. (34.76 g, 77.04%)

出典と根拠

ORDレコード
ord-be361221d8954c20ad0e2af6c64cbc63
出典データセット
uspto-grants-2005_02
特許番号
US06855745B2

反応ノート

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