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

HRID 1611414노트

반응식

HRID 1611414 반응식
[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]

참가 물질

7

반응물 4

HCID 700EthanolamineHCID 6417Pivalic acidHCID 80352,5-HexanedioneHCID 22168748HCID 22168748, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

반응 조건

온도
115 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-a25a12d337ab49a49afe1cbda1892f18
출처 데이터셋
uspto-grants-2006_01
특허 번호
US06987123B2

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