5-Hexene-2-one → 2-[4-(Trifluoromethyl)phenyl]hex-5-en-2-ol

HRID 718018Notizen

Reaktionsgleichung

[CH3:1][C:2](=[O:7])[CH2:3][CH2:4][CH:5]=[CH2:6].[F:8][C:9]([F:19])([F:18])[C:10]1[CH:15]=[CH:14][C:13]([Mg]Br)=[CH:12][CH:11]=1>O1CCCC1.C(OCC)(=O)C>[F:8][C:9]([F:19])([F:18])[C:10]1[CH:15]=[CH:14][C:13]([C:2]([OH:7])([CH2:3][CH2:4][CH:5]=[CH2:6])[CH3:1])=[CH:12][CH:11]=1

Komponenten

Reaktionsbedingungen

Temperatur: 70 °C

Versuchsvorschrift

A solution of hex-5-en-2-one (1.00 g, 10.2 mmol) in tetrahydrofuran (3 mL) was added to [4-(trifluoromethyl)phenyl]magnesium bromide (0.26 M solution in tetrahydrofuran, 50 mL, 13 mmol) at 0° C. After 15 minutes at 0° C., the reaction mixture was heated at 70° C. for 18 hours, then cooled to room temperature, diluted with ethyl acetate, and washed with saturated aqueous ammonium chloride solution, with water, and with saturated aqueous sodium chloride solution. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. Purification via silica gel chromatography (Gradient: 10% to 30% ethyl acetate in heptane) afforded the product as a dark gold oil. Yield: 1.86 g, 7.61 mmol, 75%. 1H NMR of crude product (400 MHz, CDCl3), characteristic peaks: δ 7.59 (br AB quartet, JAB=8 Hz, ΔνAB=19 Hz, 4H), 5.74-5.85 (m, 1H), 4.93-5.01 (m, 2H), 1.59 (s, 3H).

Aufarbeitung

temperaturecooled to room temperature
washwashed with saturated aqueous ammonium chloride solution, with water
dry with materialThe organic layer was dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customPurification via silica gel chromatography (Gradient: 10% to 30% ethyl acetate in heptane)

Quellen und Nachweise

ORD-Eintrag: ord-7b0a03df36a549b1891ad5966170cdda
Quelldatensatz: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09193726B2

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