6-m-Methoxyphenylhex-1-en-3-one → HCID 21485528, compound

HRID 1077147Notes

Reaction equation

HRID 1077147 reaction equation
[CH2:1]([CH:4]1[C:8](=[O:9])[CH2:7][CH2:6][C:5]1=[O:10])[CH2:2][CH3:3].[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH2:19][CH2:20][CH2:21][C:22](=[O:25])[CH:23]=[CH2:24])[CH:16]=[CH:17][CH:18]=1>[OH-].[K+]>[CH2:1]([C:4]1([CH2:24][CH2:23][C:22](=[O:25])[CH2:21][CH2:20][CH2:19][C:15]2[CH:16]=[CH:17][CH:18]=[C:13]([O:12][CH3:11])[CH:14]=2)[C:8](=[O:9])[CH2:7][CH2:6][C:5]1=[O:10])[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 107982386-m-Methoxyphenylhex-1-en-3-oneHCID 15253957HCID 15253957, compound

Product 1

HCID 21485528HCID 21485528, compoundYield 79.6%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

Condense 2-propylcyclopentane-1,3-dione (13.1 g) in 0.12% methanolic potassium hydroxide solution (90 cc) with 6-m-methoxyphenylhex-1-en-3-one (19.0 g), to obtain crude 2-n-propyl-2-(6-m-methoxyphenyl-3-oxohexyl)cyclopentane-1,3-dione (25.5 g). Submit this Michael condensation product (23.4 g) to double cyclodehydration by heating with toluene-p-sulfonic acid, and distil the product at 200°/10-4 mm; crystallize the distillate from ethanol to obtain the tetracyclic diene ketone 13β-propyl-3-methoxygona-1,3,5(10),8,14-pentaen-17-one, m.p. 82°-84°; ultraviolet absorption peak at 310 mμ (ε24,700).

Sources & evidence

ORD record
ord-de2ca069297e44698726db2e3c680f7a
Source dataset
uspto-grants-1976_05
Patent number
US03959322

Reaction notes

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