Dimethylformamide → HCID 19701592, Verbindung

HRID 862070

Reaktionsgleichung

Reaktionsgleichung von HRID 862070
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][Si:13]([CH3:16])([CH3:15])[CH3:14])=[CH:7][CH:6]=1.CCCCC.C([Li])(C)(C)C.CN([CH:30]=[O:31])C.C(OCC)(=O)C>C(OCC)C.O>[CH3:15][Si:13]([CH3:14])([CH3:16])[C:12]#[C:11][C:8]1[CH:9]=[CH:10][C:5]([O:4][CH2:3][O:2][CH3:1])=[C:6]([CH:7]=1)[CH:30]=[O:31]

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 10657368HCID 10657368, VerbindungHCID 178446069HCID 178446069, Verbindung

Produkt 1

HCID 19701592HCID 19701592, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A solution of 4-(2-trimethylsilylethynyl)phenol methoxymethyl ether (6.08 g) in diethyl ether (450 ml) was cooled to -78° C., to which was added dropwise, under argon atmosphere, a 1.7M t-butyl lithium pentane solution (18 ml), and the mixture was stirred for one hour at the same temperature. To the reaction mixture was then added dropwise DMF(5 ml), followed by warming up to room temperature and stirring overnight. To the reaction mixture were added ethyl acetate and water, which was subjected to extraction. The organic layer was washed (a saturated aqueous saline solution) and dried (anhydrous magnesium sulfate), followed by distilling off the solvent under reduced pressure. The residue was purified by means of a silica gel column chromatography (eluted with ethyl acetate/hexane) to give 5-(2-trimethylsilylethynyl)-2-methoxymethoxybenzaldehyde (5.29 g) (Compound B-27). The physical properties are shown in Table 8.

Aufarbeitung

  1. additionwas added dropwise, under argon atmosphere
  2. extractionwas subjected to extraction
  3. washThe organic layer was washed (a saturated aqueous saline solution) and
  4. dry with materialdried (anhydrous magnesium sulfate)
  5. distillationby distilling off the solvent under reduced pressure
  6. customThe residue was purified by means of a silica gel column chromatography (eluted with ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-01eb2cf2a43c4d479d27f41b864bad98
Quelldatensatz
uspto-grants-1998_02
Patentnummer
US05716971

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