Hydrochloric Acid → 4-Hydroxy-3-methyl-2-(2-propynyl)-2-cyclopentene-1-one

HRID 1980612

반응식

HRID 1980612 반응식
[CH3:1][C:2]1[O:6][C:5]([CH:7]([CH2:9][C:10]#[CH:11])O)=[CH:4][CH:3]=1.[OH-:12].[Na+].Cl.[Cl-].[Na+]>O>[CH2:3]([C:4]1[C:5](=[O:6])[CH2:7][CH:9]([OH:12])[C:10]=1[CH3:11])[C:2]#[CH:1]

참가 물질

6

반응물 4

HCID 313Hydrochloric Acid3회HCID 5234Sodium ChlorideHCID 14798Sodium Hydroxide4회HCID 98774181-(5-Methylfuran-2-yl)but-3-yn-1-ol

생성물 1

HCID 129182064-Hydroxy-3-methyl-2-(2-propynyl)-2-cyclopentene-1-one

시약·촉매·용매 1

HCID 962Water용매

실험 절차

In a reaction vessel, water (200 ml) and 5-methyl-2-furylpropargylcarbinol (5 g) were charged, and the pH value was adjusted to 4 with an aqueous 1/3N NaOH solution and an aqueous 1/3N HCl solution. The temperature was elevated to 100° C. to reflux, and the mixture was stirred under reflux for 16 hours while maintaining the pH value of 3.8 to 4.1 by the addition of an aqueous 1/3N NaOH solution and an aqueous 1/3N HCl solution. Then, the pH value was adjusted to 8.0 with an aqueous 1/3N NaOH solution, and stirring under reflux was continued for 4 hours while maintaining the pH value of 7.5 to 8.0 by the addition of an aqueous 1/3N NaOH solution and an aqueous 1/3N HCl solution. After cooling, sodium chloride (70 g) was added, and the mixture was extracted with toluene (100 ml) four times. The extract was concentrated at 60° C. under reduced pressure to remove toluene, whereby an oily substance (4.7 g) was obtained. The crude product was purified by column chromatography with silica gel (60 g) (developing solvent, ethyl acetate-n-hexane (1:2 by volume)) to obtain 2-propargyl-3-methyl-4-hydroxy-2-cyclopentenone (3.4 g). Yield, 68%.

후처리

  1. customwas elevated to 100° C.
  2. temperatureto reflux
  3. temperatureunder reflux for 16 hours
  4. temperaturewhile maintaining the pH value of 3.8 to 4.1
  5. stirringstirring
  6. temperatureunder reflux
  7. temperaturewhile maintaining the pH value of 7.5 to 8.0
  8. temperatureAfter cooling
  9. extractionthe mixture was extracted with toluene (100 ml) four times
  10. concentrationThe extract was concentrated at 60° C. under reduced pressure
  11. customto remove toluene, whereby an oily substance (4.7 g)
  12. customwas obtained
  13. customThe crude product was purified by column chromatography with silica gel (60 g) (developing solvent, ethyl acetate-n-hexane (1:2 by volume))

출처 및 근거

ORD 기록
ord-18f74f3775d64eb1acb30eef25f9a6bf
출처 데이터셋
uspto-grants-1985_04
특허 번호
US04510329

연결된 노트

불러오는 중…