반응 #745430

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methyl 3,5-dibromobenzoate

2-[(1E)-3-methoxyprop-1-en-1-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

triphenylphosphine

sodium carbonate

→

title compound

Methyl 3,5-bis[(1E)-3-methoxyprop-1-en-1-yl]benzoate

용매

ether

DMF

반응 조건

후처리

1. 1
   온도After cooling to rt
2. 2
   추출The organic extract
3. 3
   세척was washed with water, brine
4. 4
   건조dried over MgSO4
5. 5
   농축concentrated in vacuo
6. 6
   기타The crude product was purified by flash column chromatography (SiO2, 20% EtOAc in Hex)

실험 절차

To a solution of methyl 3,5-dibromobenzoate (1 eq.) from the previous step in DMF (0.2 M) was added 2-[(1E)-3-methoxyprop-1-en-1-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2.1 eq.), palladium acetate (10 mol %), triphenylphosphine (30 mol %), and 2.0 M aqueous sodium carbonate solution (5 eq.). The reaction was heated to 80° C. and stirred for 3 h. After cooling to rt, the reaction was diluted with ether. The organic extract was washed with water, brine, dried over MgSO4, and concentrated in vacuo. The crude product was purified by flash column chromatography (SiO2, 20% EtOAc in Hex) to afford the title compound as an oil.

출처