Acetic Anhydride → 1-(4-Ethoxyphenyl)-1-(2-fluoro-2-(methoxycarbonyl)ethenyl)cyclopropane

HRID 963802Notes

Reaction equation

HRID 963802 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2([CH:13]=O)[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)[CH3:2].C(OC(=O)C)(=O)C.Cl[C:23](Cl)([F:28])[C:24]([O:26][CH3:27])=[O:25]>[Zn].[Cu]Cl.O1CCCC1>[CH2:1]([O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2([CH:13]=[C:23]([F:28])[C:24]([O:26][CH3:27])=[O:25])[CH2:11][CH2:12]2)=[CH:8][CH:9]=1)[CH3:2]

Participants

7

Reactant 3

HCID 7918Acetic AnhydrideHCID 135372521-(4-Ethoxyphenyl)cyclopropane-1-carbaldehydeHCID 13612258Methyl 2,2-dichloro-2-fluoroacetate

Product 1

HCID 542883691-(4-Ethoxyphenyl)-1-(2-fluoro-2-(methoxycarbonyl)ethenyl)cyclopropaneYield 62.7%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 62652Cuprous chlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The method of Example 1 was repeated using zinc powder (4.1 g), copper (I) chloride (0.63 g), molecular sieve 4A (4.2 g), tetrahydrofuran (72 ml), 1-(4-ethoxyphenyl)-1-formylcyclopropane (4.7 g), acetic anhydride (2.6 ml) and methyl dichloro-fluoroacetate (3.3 g) to yield the title compound (3.4 g, 52%).

Sources & evidence

ORD record
ord-6dfe3b85286e4a63a3fc004dc93e6424
Source dataset
uspto-grants-1998_06
Patent number
US05763700

Reaction notes

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