2-Chloromethyl 2-(trimethylsilyl)ethyl ether → HCID 86745670, Verbindung

HRID 1030283Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1030283
[CH2:1]([C:5]1[NH:6][C:7]([C:14]([O:16][CH3:17])=[O:15])=[C:8]([C:10]([O:12][CH3:13])=[O:11])[N:9]=1)[CH2:2][CH2:3][CH3:4].CC(C)([O-])C.[K+].[CH3:24][Si:25]([CH3:32])([CH3:31])[CH2:26][CH2:27][O:28][CH2:29]Cl>CN(C=O)C.C1COCC1>[CH3:24][Si:25]([CH3:32])([CH3:31])[CH2:26][CH2:27][O:28][CH2:29][N:9]1[C:8]([C:10]([O:12][CH3:13])=[O:11])=[C:7]([C:14]([O:16][CH3:17])=[O:15])[N:6]=[C:5]1[CH2:1][CH2:2][CH2:3][CH3:4]

Komponenten

6

Edukt 3

HCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 14955796Dimethyl 2-butyl-1H-imidazole-4,5-dicarboxylateHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 86745670HCID 86745670, VerbindungAusbeute 106 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

The diester 1 from Step (a) (23 g, MW 240, 0.096 mol) was dissolved in 300 ml DMF. Potassium t-butoxide (100 ml of a 1M solution in dry THF) was added through a syringe. The solution was stirred for 15 min at 25° C. [2-(trimethylsilyl)ethoxy]methyl chloride (SEM-chloride, 18.6 ml, 1.1 eq, MW 166, d 0.94) was added and a precipitate instantly formed. The reaction was stirred for 90 min at 25° C. The solvent was removed and the residue partitioned between ethyl acetate and water. The organic extract was dried over K2CO3 and concentrated. By TLC (SiO2, MeOH-CHCl3 /1-10) a single major spot was observed. This crude product (38 g, 106% yield) was used in subsequent steps without further purification.

Aufarbeitung

  1. additionwas added
  2. customa precipitate instantly formed
  3. customThe solvent was removed
  4. customthe residue partitioned between ethyl acetate and water
  5. extractionThe organic extract
  6. dry with materialwas dried over K2CO3
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-083931cdec5a451692565c758970fdeb
Quelldatensatz
uspto-grants-1992_04
Patentnummer
US05104891

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