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

HRID 868373

Reaction equation

HRID 868373 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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°.

Workup

  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°

Sources & evidence

ORD record
ord-1d664d7a2fbd4c19bec6162263fba5f7
Source dataset
uspto-grants-1988_10
Patent number
US04778903

Linked notes

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