Sodium hydride → 4-[[[(1,1-Dimethylethyl)dimethylsilyl]oxy]methyl]thiazole

HRID 1792752Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1792752
[H-].[Na+].CC1N=NC(N2CCC(CCO)CC2)=CC=1.Cl[C:20]1[S:21][CH:22]=[C:23]([CH2:25][O:26][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])[N:24]=1>C(COC)OC.CCOCC>[Si:27]([O:26][CH2:25][C:23]1[N:24]=[CH:20][S:21][CH:22]=1)([C:30]([CH3:33])([CH3:31])[CH3:32])([CH3:28])[CH3:29]

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 149892172-(1-(6-Methylpyridazin-3-YL)piperidin-4-YL)ethanolHCID 220242412-Chloro-4-t-butyldimethylsilyloxymethylthiazole

Produkt 1

HCID 667166624-[[[(1,1-Dimethylethyl)dimethylsilyl]oxy]methyl]thiazoleAusbeute 81,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel2×

Versuchsvorschrift

A suspension of sodium hydride (60%, 135 mg, 3.4 mmol) and 1-(6-methyl-3-pyridazinyl)-4-(2-hydroxyethyl)-piperidine (250 mg, 1.1 mmol) in dimethoxyethane (DME; 4 ml) was stirred at room temperature for 2 hr. A solution of 2-chloro-4-t-butyldimethylsilyloxymethylthiazole (385 mg, 1.46 mmol) in DME (1 ml) was added and the mixture stirred at reflux under argon for 5 hr then at room temperature overnight. The mixture was diluted with ether, filtered and then concentrated. The residue was chromatographed on silica gel (25 g; eluent 30%-50% ethyl acetate/hexane) to give 2-1 -(6-methyl-3-pyridazinyl)-4-piperidinylethyl-1-oxy)-4t-butyldimethylsilyloxymethylthiazole (274 mg, 54%), 1H nmr, 0.11 (s, 6H), 0.94 (s, 9H), 1.3-1.87 (m, 7H), 2.58 (s, 3H), 2.93 (t, 2H), 4.31-4.35 (m, 2H), 4.48 (t, 2H), 4,64 (s, 2H), 6.51 (s, 1H), 6.93 (d, 1H), 7.11 (d, 1H).

Aufarbeitung

  1. stirringthe mixture stirred
  2. temperatureat reflux under argon for 5 hr
  3. customat room temperature
  4. customovernight
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel (25 g; eluent 30%-50% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-67d1d9cf48ee4a3e80ffd966c1a31e3d
Quelldatensatz
uspto-grants-2006_07
Patentnummer
US07078403B1

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