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Isomerization of methyl E-2 to Z-2

EK Eiji Kudo
KS Kota Sasaki
SK Shiori Kawamata
KY Koji Yamamoto
TM Tetsuro Murahashi
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To a solution of [Pd2(CH3CN)6][BF4]2 (1, 126.5 mg, 2.00 × 10−1 mmol) in CH3NO2 was added methyl (E)-5-methylhexa-2,4-dienoate (E-2, 28.0 mg, 2.00 × 10−1 mmol) and stirred at room temperature for 30 min. The reaction mixture was cooled to −30 °C and COT (41.7 mg, 4.00 × 10−1 mmol, 2 equiv.) was added. After stirring 15 min, the mixture was diluted with diethyl ether, and filtered through a silica gel pad. The solvent was removed in vacuo and the residue was purified by a silica gel column chromatography to give methyl (Z)-5-methylhexa-2,4-dienoate (Z-2) as colorless oil (22.4 mg, 1.60 × 10−1 mmol, 80% yield, E:Z = <1:>99).

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