Triphenylphosphine → 3-(3-Acetamidophenylethynyl)-3-(3-cyclopentyloxy-4-methoxyphenyl)-cyclohexan-1-one

HRID 442710

Reaktionsgleichung

[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:15]3([C:22]#[CH:23])[CH2:20][CH2:19][CH2:18][C:17](=[O:21])[CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:24]([NH:27][C:28]1[CH:29]=[C:30](I)[CH:31]=[CH:32][CH:33]=1)(=[O:26])[CH3:25].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(N(CC)CC)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[C:24]([NH:27][C:28]1[CH:33]=[C:32]([C:23]#[C:22][C:15]2([C:9]3[CH:10]=[CH:11][C:12]([O:13][CH3:14])=[C:7]([O:6][CH:1]4[CH2:2][CH2:3][CH2:4][CH2:5]4)[CH:8]=3)[CH2:20][CH2:19][CH2:18][C:17](=[O:21])[CH2:16]2)[CH:31]=[CH:30][CH:29]=1)(=[O:26])[CH3:25]

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

To a solution of the compound from Example 3 (E1) (0.2 g, 0.64 mmol) and 3-acetamido-1-iodobenzene (0.17 g, 0.64 mmol) in triethylamine (5 mL) under an argon atmosphere was added trace tetrakis(triphenylphosphine)palladium(0), copper(I) iodide and triphenylphosphine. The mixture was heated at 80° C. for 0.3 h, was cooled to room temperature and was concentrated in vacuo. The residue was purified by flash chromatography, eluting with 1:1 hexanes/ethyl acetate, to provide the title compound as tan solid (0.17 g, 60%), m.p. 58°-60° C.

Aufarbeitung

temperaturewas cooled to room temperature
concentrationwas concentrated in vacuo
customThe residue was purified by flash chromatography
washeluting with 1:1 hexanes/ethyl acetate

Quellen und Nachweise

ORD-Eintrag: ord-108349e34c914da5977b248d087fe4ae
Quelldatensatz: uspto-grants-1999_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05891883

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