1-Naphthaldehyde → 1-(1-Naphthyl)-1-propanol

HRID 2293677

Reaktionsgleichung

[CH2:1]([Mg]Br)[CH3:2].[C:5]1([CH:15]=[O:16])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1>O1CCCC1>[C:5]1([CH:15]([OH:16])[CH2:1][CH3:2])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

To a flame-dried flask containing 8.0 mL of dry tetrahydrofuran under an argon atmosphere cooled to -78° C. Is added 4.0 mL (3.0 M) of a solution of ethylmagnesium bromide in tetrahydrofuran. The stirrable mixture is treated with a solution of 1.36 g of commercially available 1-naphthaldehyde in 4.0 mL of tetrahydrofuran with a 2 mL rinse. The reaction is stirred at -78° C. for 5 minutes then warmed to room temperature. After 1 hour the mixture is re-cooled to 0° C., carefully quenched with saturated ammonium chloride, and diluted with diethyl ether. The layers are separated; organic phase washed with brine, dried (magnesium sulfate), and concentrated under reduced pressure. The residue is flash column chromatographed using 25% ethyl acetate in hexane to give 1.76 g of the title product as a pale pink oil.

Aufarbeitung

washrinse
temperaturethen warmed to room temperature
temperatureAfter 1 hour the mixture is re-cooled to 0° C.
customcarefully quenched with saturated ammonium chloride
additiondiluted with diethyl ether
customThe layers are separated
washorganic phase washed with brine
dry with materialdried (magnesium sulfate)
concentrationconcentrated under reduced pressure
customchromatographed

Quellen und Nachweise

ORD-Eintrag: ord-a3bae3ce05c84673a4f3379e3f30c941
Quelldatensatz: uspto-grants-1997_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05686486

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