Ethanolamine → 1-(2-Hydroxyethyl)-2,5-dimethylpyrrole

HRID 1611414ノート

反応式

HRID 1611414 の反応式
[CH3:1][C:2](=O)[CH2:3][CH2:4][C:5](=O)[CH3:6].[CH2:9]([CH2:11][NH2:12])[OH:10].C(O)(=O)C(C)(C)C.CCCCCCC.O1CCCC1.C1(C)C=CC=CC=1>ClCCl.O>[OH:10][CH2:9][CH2:11][N:12]1[C:2]([CH3:1])=[CH:3][CH:4]=[C:5]1[CH3:6]

参加物

7

反応物 4

HCID 700EthanolamineHCID 6417Pivalic acidHCID 80352,5-HexanedioneHCID 22168748HCID 22168748、化合物

生成物 1

HCID 959631-(2-Hydroxyethyl)-2,5-dimethylpyrrole

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
115 °C

実験手順

A mixture of hexan-2,5-dione (5 g), ethanol amine (26.7 g) and pivalic acid (23.26 g) in a solvent mixture containing n-heptane: tetrahydrofuran: toluene (4:1:1, 50 mL) was refluxed with stirring at 110-120° C. Water formed during the reaction was removed azeotropically during 3 to 4 hrs. The reaction mixture was cooled and the solvent was removed. The residue obtained was dissolved in dichloromethane (30 mL), washed with saturated sodium bicarbonate solution (30 mL), water (30 mL), and then with brine (30 mL), dried (Na2SO4) and the solvent was evaporated. The crude compound obtained as an oily mass, was purified by column chromatography (silica gel 100-200), using ethyl acetate:hexane (2:8) as an eluent to obtain the title compound.

後処理

  1. temperaturewas refluxed
  2. customwas removed azeotropically during 3 to 4 hrs
  3. temperatureThe reaction mixture was cooled
  4. customthe solvent was removed
  5. customThe residue obtained
  6. washwashed with saturated sodium bicarbonate solution (30 mL), water (30 mL)
  7. dry with materialwith brine (30 mL), dried (Na2SO4)
  8. customthe solvent was evaporated
  9. customThe crude compound obtained as an oily mass
  10. customwas purified by column chromatography (silica gel 100-200)

出典と根拠

ORDレコード
ord-a25a12d337ab49a49afe1cbda1892f18
出典データセット
uspto-grants-2006_01
特許番号
US06987123B2

反応ノート

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