Triethylamine → 1-(2-Cyclopropylethynyl)-4-methoxybenzene

HRID 45275

Reaktionsgleichung

Reaktionsgleichung von HRID 45275
C1(C#C)CC1.[CH:6]1([C:9]#[C:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[CH2:8][CH2:7]1.IC1C=CC(OC)=CC=1.C(N(CC)CC)C>O1CCCC1.[Cu]I>[CH:6]1([C:9]#[C:10][C:11]2[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=2)[CH2:8][CH2:7]1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 696764-IodoanisoleHCID 866035461-Cyclopropylethynyl-4-methoxy-benzene Cyclopropylethyne

Produkt 1

HCID 586098031-(2-Cyclopropylethynyl)-4-methoxybenzeneAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

1-Cyclopropylethynyl-4-methoxy-benzene Cyclopropylethyne (15 g, 0.22 mol) was slowly added to a mixture of 4-iodoanisole (30 g, 0.13 mol), copper (I) iodide (1.2 g, 0.0063 mol), and triethylamine (30 g, 0.30 mol) in tetrahydrofuran (THF, 400 mL). After being stirred for 4 hours, the resulting precipitate was filtered and washed with THF. The combined filtrate was evaporated to dryness and the residue was purified by column chromatography to afford 1-cyclopropylethynyl-4-methoxy-benzene as a yellow oil (15 g, 0.087 mol, 67%). NMR (CDCl3) δ 7.31 (d, J=8.8 Hz, 2 H), 6.80 (d, J=8.8 Hz, 2H), 3.79 (s, 3H), 1.43 (m, 1H), 0.85 (m, 2H), 0.78 (m, 2H).

Aufarbeitung

  1. filtrationthe resulting precipitate was filtered
  2. washwashed with THF
  3. customThe combined filtrate was evaporated to dryness
  4. customthe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-9a5a8d6383894334bbc0af4ce4de09ce
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541453B2

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