Chloride → 1-{4-[(4-Butylphenyl)ethynyl]phenyl}-1-pentanol

HRID 551912

Reaktionsgleichung

[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[Cl-].Cl>C1COCC1>[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:20]=[CH:19][C:16]([CH:17]([OH:18])[CH2:5][CH2:1][CH2:2][CH3:3])=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4]

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

To a cold (−78° C.) solution of 4-[(4-butylphenyl)ethynyl]benzaldehyde (2.6 g, 10.0 mmol, intermediate which may be obtained according to methods disclosed in EP03103780.7) in anhydrous THF (40 mL) was added dropwise a solution of butylmagnesim chloride in THF (7.5 mL, 15.00 mmol, 2N). The resulting solution was stirred at −78° C. for 1 hr, then allowed to reach rt and stirred at rt for 5 hrs. An aqueous solution of HCl (10 mL, 1N) was added and the resulting mixture was extracted with Et2O (3×). The combined organic layers were washed with water and brine, dried over MgSO4 and the solvents were removed under reduced pressure to give 2.45 g (76%) of the title compound as a white solid. HPLC, Rt: 5.4 min (purity: 100%). 1H NMR (CDCl3) δ: 7.51 (d, J=8.2 Hz, 2H), 7.44 (d, J=8.3 Hz, 2H), 7.32 (d, J=8.2 Hz, 2H), 7.16 (d, J=8.3 Hz, 2H), 4.68 (t, J=7.2 Hz, 1H), 2.62 (t, J=7.9 Hz, 2H), 1.88-1.19 (m, 10H), 0.98-0.83 (m, 6H).

Aufarbeitung

customto reach rt
stirringstirred at rt for 5 hrs
extractionthe resulting mixture was extracted with Et2O (3×)
washThe combined organic layers were washed with water and brine
dry with materialdried over MgSO4
customthe solvents were removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag: ord-bb3b123969ea4b92af8ac04b674e7a78
Quelldatensatz: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07947851B2

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