2-Butyl-1,3-cyclopentanedione → 13beta-Butyl-3-methoxygona-1,3,5(10),8,14-pentaen-17-one

HRID 1077148Notes

Reaction equation

HRID 1077148 reaction equation
[CH2:1]([CH:5]1[C:9](=[O:10])[CH2:8][CH2:7][C:6]1=O)[CH2:2][CH2:3][CH3:4].[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH2:20][CH2:21][CH2:22][C:23](=O)[CH:24]=[CH2:25])[CH:17]=[CH:18][CH:19]=1>[OH-].[K+]>[CH2:1]([C@:5]12[CH2:6][CH2:7][C:8]3[C:17]4[CH:18]=[CH:19][C:14]([O:13][CH3:12])=[CH:15][C:16]=4[CH2:20][CH2:21][C:22]=3[C:23]1=[CH:24][CH2:25][C:9]2=[O:10])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 5744932-Butyl-1,3-cyclopentanedioneHCID 107982386-m-Methoxyphenylhex-1-en-3-one

Product 1

HCID 5412707213beta-Butyl-3-methoxygona-1,3,5(10),8,14-pentaen-17-oneYield 32.5%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

Condense n-butylcyclopentane-1,3-dione (2.8 g) in 0.12% methanolic potassium hydroxide solution (8 cc) with 6-m-methoxyphenylhex-1-en-3-one (5 g) by heating the mixture at 80° for 10 hours. Evaporate the solvent under reduced pressure and heat the residue with toluene-p-sulfonic acid (2 g) in benzene (50 cc) for 45 minutes using a Dean-Stark trap to effect double cyclodehydration. Add ether to the cooled reaction mixture, and evaporate the washed and solution; recrystallize ether solution;recrystallize the residue from ethanol to obtain 13β-butyl-3-methoxygona-1,3,5(10),8,14-pentaen-17-one (1.9 g), m.p. 53°-55°; ultraviolet absorption peak at 312 mμ (ε29,200).

Workup

  1. temperatureby heating the mixture at 80° for 10 hours
  2. customEvaporate the solvent under reduced pressure
  3. temperatureheat the residue with toluene-p-sulfonic acid (2 g) in benzene (50 cc) for 45 minutes
  4. customAdd ether to the cooled reaction mixture
  5. customevaporate the
  6. washwashed

Sources & evidence

ORD record
ord-3fb87f44379d40289e47b41dd321c49d
Source dataset
uspto-grants-1976_05
Patent number
US03959322

Reaction notes

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