Methyl 4-pentynoate → 5-(4-Trifluoromethoxy-phenyl)-pent-4-ynoic acid methyl ester

HRID 751210Notes

Reaction equation

HRID 751210 reaction equation
[CH3:1][O:2][C:3](=[O:8])[CH2:4][CH2:5][C:6]#[CH:7].I[C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=1>>[CH3:1][O:2][C:3](=[O:8])[CH2:4][CH2:5][C:6]#[C:7][C:10]1[CH:11]=[CH:12][C:13]([O:16][C:17]([F:18])([F:19])[F:20])=[CH:14][CH:15]=1

Participants

3

Reactant 2

HCID 543061Methyl 4-pentynoateHCID 27772941-Iodo-4-(trifluoromethoxy)benzene

Product 1

HCID 688211875-(4-Trifluoromethoxy-phenyl)-pent-4-ynoic acid methyl ester

Procedure

In analogy to the procedure described for example 8 a], pent-4-ynoic acid methyl ester (W. D. Wulff, S. J. McCallum, F. A. Kunng, J. Am. Chem. Soc. 1988, 110, 7419-7434) was reacted with 1-iodo-4-trifluoromethoxy-benzene in the presence of PdCl2(Ph3P)2 and cuprous iodide to give the title compound as brown oil.

Sources & evidence

ORD record
ord-6f8b8e5d3ff44c82b8b592663c8fe2c6
Source dataset
uspto-grants-2008_07
Patent number
US07405236B2

Reaction notes

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