Acetic Acid → 1H-Pyrrol-1-ylacetic acid

HRID 26580

반응식

HRID 26580 반응식
C(O)(=O)C.C([O-])(=O)C.[Na+].[NH2:10][CH2:11][C:12]([OH:14])=[O:13].CO[CH:17]1[CH2:21][CH2:20][CH:19](OC)O1>C1(C)C=CC=CC=1>[N:10]1([CH2:11][C:12]([OH:14])=[O:13])[CH:17]=[CH:21][CH:20]=[CH:19]1

참가 물질

6

반응물 4

HCID 176Acetic Acid2회HCID 750GlycineHCID 790982,5-DimethoxytetrahydrofuranHCID 517045Sodium Acetate

생성물 1

HCID 2420271H-Pyrrol-1-ylacetic acid수율 33.6%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To a 1 liter flask fitted with a condenser, a magnetic stirrer and a nitrogen inlet tube is added acetic acid (glacial, 300 ml) and sodium acetate (32.8g; 0.4 mole). The system is purged with nitrogen and a positive nitrogen pressure is maintained. Then glycine (15.0g; 0.2 mole) is added and the solution is heated to reflux. To the refluxing, clear solution is added 2,5-dimethoxytetrahydrofuran (29 ml, 0.2 mole) over a period of 2 - 3 minutes; refluxing is continued an additional 2 minutes. The reaction mixture is cooled in an ice bath and most of the acetic acid is removed under vacuum. The residue is taken up in water and extracted with four portions of ether. The ether extracts are washed with water, dried over anhydrous magnesium sulfate, filtered and the ether is evaporated to yield a slurry. The slurry is taken up into toluene, filtered through celite and crystallized by cooling to give 8.41g. (33.6%) of the title compound. M.P. 88°-90° C.

후처리

  1. customTo a 1 liter flask fitted with a condenser, a magnetic stirrer and a nitrogen inlet tube
  2. customThe system is purged with nitrogen
  3. temperaturea positive nitrogen pressure is maintained
  4. temperaturethe solution is heated to reflux
  5. temperaturerefluxing
  6. customis removed under vacuum
  7. extractionextracted with four portions of ether
  8. washThe ether extracts are washed with water
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. customthe ether is evaporated
  12. customto yield a slurry
  13. filtrationfiltered through celite
  14. customcrystallized
  15. temperatureby cooling
  16. customto give 8.41g

출처 및 근거

ORD 기록
ord-cf6ba1b87c0b47b1a41340b554058056
출처 데이터셋
uspto-grants-1979_04
특허 번호
US04150224

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