Dimethylformamide → HCID 20077568, Verbindung

HRID 1587799Notizen

Reaktionsgleichung

[Si:1]([C:8]1[S:9][CH:10]=[CH:11][N:12]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C([Li])CCC.CN(C)[CH:20]=[O:21].[Cl-].[NH4+]>CCOCC>[Si:1]([C:8]1[S:9][C:10]([CH:20]=[O:21])=[CH:11][N:12]=1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:2])[CH3:3]

Komponenten

Reaktionsbedingungen

Temperatur: -40 °C

Versuchsvorschrift

A solution of compound Q (40 g) in ether (100 ml) was added dropwise to a solution of n-butyllithium (1.6M solution in hexane, 138 ml) in ether (300 ml) at -70° C. under an atmosphere of argon. The mixture was stirred for 1 hour at this temperature and then N,N-dimethylformamide (30 ml) was added dropwise. The mixture was stirred for 30 minutes at -70° C., then warmed to -40° C. Excess saturated aqueous ammonium chloride solution was added and the mixture allowed to warm to ambient temperature. The layers were separated and the aqueous phase extracted three times with ether. The organic phases were combined, dried (MgSO4), and concentrated. The residue was purified by column chromatography, eluting with 25% ethyl acetate/hexane (v/v), to give 2-tert-butyldimethylsilylthiazole-5-carboxaldehyde (R) (31 g, 69% yield) as an oil; NMR: 0.32(6H,s), 0.89(9H,s), 8.55(1H,s), 10.0(1H,s).

Aufarbeitung

stirringThe mixture was stirred for 30 minutes at -70° C.
temperatureto warm to ambient temperature
customThe layers were separated
extractionthe aqueous phase extracted three times with ether
dry with materialdried (MgSO4)
concentrationconcentrated
customThe residue was purified by column chromatography
washeluting with 25% ethyl acetate/hexane (v/v)

Quellen und Nachweise

ORD-Eintrag: ord-402f9b6437c14e318efceee9d8016d15
Quelldatensatz: uspto-grants-1993_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05219874

Notizen zur Reaktion

Wird geladen…