4-Methyl-1-pentyne → HCID 68534814, Verbindung

HRID 1992887Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1992887
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5](OS(C(F)(F)F)(=O)=O)[CH:4]=1.[CH3:21][CH:22]([CH3:26])[CH2:23][C:24]#[CH:25]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([C:25]#[C:24][CH2:23][CH:22]([CH3:26])[CH3:21])[CH:4]=1

Komponenten

5

Edukt 2

HCID 1389484-Methyl-1-pentyneHCID 10710352Methyl 4-methoxy-2-(trifluoromethylsulfonyloxy)benzoate

Produkt 1

HCID 68534814HCID 68534814, VerbindungAusbeute 98,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysator

Versuchsvorschrift

Coupling of methyl 4-(methyloxy)-2-{[(trifluoromethyl)sulfonyl]oxy}benzoate (77) (1.0 g, 3.18 mmol) with 4-methyl pentyne (0.78 mL, 6.36 mmol) using Pd(PPh3)2Cl2 and CuI gave 0.77 g (98%) of compound 102 as a brown oil. 1H NMR (400 MHz, CDCl3): δ 1.06 (d, J=6.8 Hz, 6H), 1.90-2.00 (m, 1H), 2.37 (d, J=6.4 Hz, 2H), 3.83 (s, 3H), 3.87 (s, 3H), 6.82 (dd, J1=8.8 Hz, J2=2.8 Hz, 1H), 7.00 (d, J=2.7 Hz, 1H), 7.88 (d, J=8.8 Hz, 1H). LCMS (ESI): m/z 247 (M+H)+.

Quellen und Nachweise

ORD-Eintrag
ord-331e2c9ab0c64cf3b03fdf1f8391ff3a
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07649093B2

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