Triethyl 4-phosphonocrotonate, mixture of isomers → Ethyl 5-(5-methoxymethoxy-2-methoxyphenyl)hepta-2,4-dienoate

HRID 2120492Notes

Reaction equation

HRID 2120492 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([O:15][CH3:16])=[C:9]([C:11](=O)[CH2:12][CH3:13])[CH:10]=1.C(OP([CH2:25]/[CH:26]=[CH:27]/[C:28]([O:30][CH2:31][CH3:32])=[O:29])(OCC)=O)C>>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([O:15][CH3:16])=[C:9]([C:11]([CH2:12][CH3:13])=[CH:25][CH:26]=[CH:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH:10]=1

Participants

3

Reactant 2

HCID 5365783Triethyl 4-phosphonocrotonate, mixture of isomersHCID 234398213-(5-Methoxymethoxy-2-methoxyphenyl)-3-propanone

Product 1

HCID 74053077Ethyl 5-(5-methoxymethoxy-2-methoxyphenyl)hepta-2,4-dienoate

Procedure

In a manner similar to Example 63(c), by reacting 3.9 g (17 mmol) of 3-(5-methoxymethoxy-2-methoxyphenyl)-3-propanone with 8.7 g (34.8 mmol) of ethyl 4-diethylphosphonocrotonate, ethyl 5-(5-methoxymethoxy-2-methoxyphenyl)hepta-2,4-dienoate is obtained which is converted to ethyl 5-(5-hydroxy-2-methoxyphenyl)hepta-2,4-dienoate with concentrated sulphuric acid in ethanol 800 mg (17%).

Sources & evidence

ORD record
ord-61c7fdbd4ff34e7fa75c6a82a92c6e9e
Source dataset
uspto-grants-2004_02
Patent number
US06689922B1

Reaction notes

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