Pyrrolidine → 2,3-dihydro-2,2-bis(pent-4-enyl)-8-propyl-7-hydroxy-4H-1-benzopyran-4-one

HRID 2371646Notes

Reaction equation

HRID 2371646 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].[CH2:15]=[CH:16][CH2:17][CH2:18][CH2:19][C:20](=O)[CH2:21][CH2:22][CH2:23][CH:24]=[CH2:25].N1CCCC1>C1(C)C=CC=CC=1>[CH2:21]([C:20]1([CH2:19][CH2:18][CH2:17][CH:16]=[CH2:15])[CH2:13][C:11](=[O:12])[C:8]2[CH:7]=[CH:6][C:5]([OH:14])=[C:4]([CH2:3][CH2:2][CH3:1])[C:9]=2[O:10]1)[CH2:22][CH2:23][CH:24]=[CH2:25]

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 27751982',4'-Dihydroxy-3'-propylacetophenoneHCID 108448021,10-Undecadien-6-one

Product 1

HCID 151574722,3-dihydro-2,2-bis(pent-4-enyl)-8-propyl-7-hydroxy-4H-1-benzopyran-4-oneYield 84.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3.93 g (20.2 mmol) of 2,4-dihydroxy-3-propylacetophenone, 3.36 g (20.2 mmol) of the title product of Example 68, 1.44 g (20.2 mmol) of pyrrolidine, and 23.5 ml of toluene was stirred at reflux under a water separator containing 3A molecular sieves for 5 hours. The mixture was then permitted to cool, and the solvent was removed under reduced pressure. Chromatography of the residue over silica gel using 25% ethyl acetate/hexane as eluant gave the title compound (5.85 g) as a dark red oil.

Workup

  1. temperatureat reflux under a water separator
  2. temperatureto cool
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-24a2c7cb31334a569c71e346b39a4606
Source dataset
uspto-grants-1992_03
Patent number
US05093353

Reaction notes

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