Aluminium lithium hydride → (1-Formyl-2-naphthalen-2-ylethyl)carbamic acid tert-butyl ester

Reaktionsgleichung

[C:1]([O:5][C:6](=[O:26])[NH:7][CH:8]([C:20](=[O:25])NCOC)[CH2:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[C:1]([O:5][C:6](=[O:26])[NH:7][CH:8]([CH:20]=[O:25])[CH2:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=1)([CH3:2])([CH3:4])[CH3:3]

Komponenten

Reaktionsbedingungen

Temperatur: -55 °C

Versuchsvorschrift

To a solution of [1-(methoxymethylcarbamoyl)-2-naphthalen-2-ylethyl]carbamic acid tert-butyl ester, 67, (5.0 g, 13.4 mmol) in THF (40 mL) at −30° C. to −25° C. is added LAH (16.7 mL of a 1M solution in THF) over about 10 minutes and the reaction is then cooled to −55° C. and the stirring is continued for 3 hours. After cooling to −60° C., the reaction is quenched by the addition of citric acid in methanol (1:1 by weight). During quenching the temperature is maintained at about −45° C. The mixture is then allowed to warm to room temperature and partitioned between EtOAc and water and the water phase extracted again with EtOAc. The organic phases are combined and washed with sat NaCl, dried and concentrated in vacuo to afford the crude aldehyde as a white solid which is used without further purification.

Aufarbeitung

temperatureAfter cooling to −60° C.
customthe reaction is quenched by the addition of citric acid in methanol (1:1 by weight)
customDuring quenching the temperature
temperatureis maintained at about −45° C
temperatureto warm to room temperature
custompartitioned between EtOAc and water
extractionthe water phase extracted again with EtOAc
washwashed with sat NaCl
customdried
concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-3bcc3ad5af944641a39f0ca173a215de
Quelldatensatz: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07087759B2

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