Ethyl Acetate → HCID 19917090, 화합물

반응식

[S:1]1[CH:5]=[CH:4][C:3](/[CH:6]=[CH:7]/[CH:8]=[CH:9]/[CH2:10]O)=[CH:2]1.P(Br)(Br)Br.C([O:19][CH2:20][CH3:21])(=O)C>>[S:1]1[CH:5]=[CH:4][C:3](/[CH:6]=[CH:7]/[CH:8]=[CH:9]/[CH2:10][C:4]2[CH:5]=[C:21]([CH:7]=[CH:6][CH:3]=2)[CH:20]=[O:19])=[CH:2]1

참가 물질

반응물 3

HCID 8857Ethyl Acetate2회

HCID 24614Phosphorus tribromide

HCID 19916935HCID 19916935, 화합물

생성물 1

HCID 19917090HCID 19917090, 화합물

실험 절차

20 mg of the resulting alcohol compound was dissolved in 1.5 ml of ethyl acetate, and under ice cooling, an ethyl acetate solution (0.5 ml) of 16.2 mg of phosphorus tribromide was added dropwise. The mixture was stirred for 1 hour, and then the solvent was evaporated. The residue was dissolved in 3 ml of toluene, and under a nitrogen atmosphere, 59 mg of 3-(tributylstannyl)benzaldehyde and 3 mg of tetrakis(triphenylphosphine)palladium were added. After the mixture was refluxed for 3 hours, 1 ml of a saturated aqueous solution of potassium fluoride was added, and the mixture was stirred at room temperature for 30 minutes. Water and ethyl acetate were added, and the organic layer separated was worked up in a customary manner. The product was purified by medium-pressure liquid chromatography [hexane/ethyl acetate=8/1] to give 7 mg of (E,E)-3-[5-(3-thienyl)-2,4-penta-dienyl]benzaldehyde as a pale yellow oil.