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

HRID 1710270Notes

Reaction equation

HRID 1710270 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-16f47fb706ab4fe987cdcc4d37f90371
Source dataset
uspto-grants-1990_08
Patent number
US04952705

Reaction notes

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