Diisobutylaluminum hydride → 2-(4-Phenylphenoxy)ethanol

HRID 459139

Reaktionsgleichung

C([O:3][C:4](=O)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:9][CH:8]=1)C.CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1>[C:10]1([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:9]=[CH:8][C:7]([O:6][CH2:5][CH2:4][OH:3])=[CH:12][CH:11]=1

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

To a solution of (Biphenyl-4-yloxy)-acetic acid ethyl ester (0.63 g, 2.46 mmol) in dry toluene (15 mL) at −78° C. was added DIBAL-H 1M in toluene (4.92 mL, 4.92 mmol). The solution was stirred at −78° C. for 1 hour, warmed to room temperature and quenched with mixture of a solution of sodium tartrate in water and ethyl acetate for 1 hour. The layers were separated and the aqueous phase further extracted with ethyl acetate. The combined organic layers were dried (MgSO4), concentrated under vacuum and the residue purified bu column chromatography (silica gel, hexanes/Ethyl acetate 4:1, Rf0.1), 48%. 1H-NMR (CDCl3, 200.15 MHz): 7.58–7.26 (m, 8H); 7.00 (d, 2H, J=8.6), 4.14 (t, 2H, J=4.6), 4.02–3.98 (m, 2H); 2.04 (t, 1H, J=5.4).

Aufarbeitung

temperaturewarmed to room temperature
customquenched with mixture of a solution of sodium tartrate in water and ethyl acetate for 1 hour
customThe layers were separated
extractionthe aqueous phase further extracted with ethyl acetate
dry with materialThe combined organic layers were dried (MgSO4)
concentrationconcentrated under vacuum
customthe residue purified bu column chromatography (silica gel, hexanes/Ethyl acetate 4:1, Rf0.1), 48%

Quellen und Nachweise

ORD-Eintrag: ord-2484a88e82574949af538a0e1631053c
Quelldatensatz: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07192982B2

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