Pyrrolidine → 3-(3,4-dihydro-7-hydroxy-2-methyl-4-oxo-8-propyl-2H-1-benzopyran-2-yl)propanoic acid

HRID 868373

반응식

HRID 868373 반응식
[CH3:1][CH2:2][CH2:3][C:4]1[C:9]([OH:10])=[C:8]([C:11]([CH3:13])=[O:12])[CH:7]=[CH:6][C:5]=1[OH:14].[C:15]([O:22]C)(=[O:21])[CH2:16][CH2:17][C:18]([CH3:20])=O.N1CCCC1>C1(C)C=CC=CC=1>[OH:14][C:5]1[CH:6]=[CH:7][C:8]2[C:11](=[O:12])[CH2:13][C:18]([CH2:17][CH2:16][C:15]([OH:22])=[O:21])([CH3:20])[O:10][C:9]=2[C:4]=1[CH2:3][CH2:2][CH3:1]

참가 물질

5

반응물 3

HCID 31268PyrrolidineHCID 69354Methyl levulinateHCID 27751982',4'-Dihydroxy-3'-propylacetophenone

생성물 1

HCID 139207383-(3,4-dihydro-7-hydroxy-2-methyl-4-oxo-8-propyl-2H-1-benzopyran-2-yl)propanoic acid

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To a mixture of 20.0 g (103 mmole) of 2,4-dihydroxy-3-propylacetophenone and 15.5 g (134 mmole) of methyl levulinate in 100 ml of dry toluene was added by syringe 21.5 ml (ca. 260 mmole) of pyrrolidine. After stirring for one hour the solution was heated on a steam bath for four hours and allowed to cool. The toluene solution was washed with water and 2N NaOH. The basic solution was acidified and extracted with diethyl ether, which in turn was extracted with saturated sodium bicarbonate. The basic aqueous extract was neutralized with dilute hydrochloric acid and again extracted with diethyl ether. After drying, the solution was concentrated at reduced pressure to an oil which crystallized to the title compound, m.p. 152°-153°.

후처리

  1. temperaturewas heated on a steam bath for four hours
  2. temperatureto cool
  3. washThe toluene solution was washed with water and 2N NaOH
  4. extractionextracted with diethyl ether, which in turn
  5. extractionwas extracted with saturated sodium bicarbonate
  6. extractionThe basic aqueous extract
  7. extractionagain extracted with diethyl ether
  8. customAfter drying
  9. concentrationthe solution was concentrated at reduced pressure to an oil which
  10. customcrystallized to the title compound, m.p. 152°-153°

출처 및 근거

ORD 기록
ord-1d664d7a2fbd4c19bec6162263fba5f7
출처 데이터셋
uspto-grants-1988_10
특허 번호
US04778903

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