Imidazole → HCID 9839780, Verbindung

HRID 1275525Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1275525
[OH:1][C:2]1[CH:15]=[CH:14][C:13]2[O:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH2:5][C:4]=2[CH:3]=1.N1C=CN=C1.[Si:21](Cl)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22]>CN(C=O)C.CN(C1C=CN=CC=1)C>[O:1]([C:2]1[CH:15]=[CH:14][C:13]2[O:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH2:5][C:4]=2[CH:3]=1)[Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22]

Komponenten

6

Edukt 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 10219823HCID 10219823, Verbindung

Produkt 1

HCID 9839780HCID 9839780, VerbindungAusbeute 79,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 2-hydroxy-9H-xanthene 3 (2.63 g, 13.28 mmole) in DMF (15 ml) was added imidazole (1.36 g, 19.9 mmole), t-butyldimethylsilyl chloride (2.4 g, 15.92 mmole) and DMAP (15 mg) successively at room temperature. The mixture was allowed to stir overnight (16 hrs) and quenched with saturated NaHCO3 solution. The aqueous layer was extracted two times with 10% EtOAc-hexanes. The combined organic layers were washed with water, dried over anhydrous Na2SO4 and concentrated. The light orange oily residue was loaded onto a silica gel plug and eluted with hexanes and then 3% EtOAc-hexanes. The relatively clean fractions of the desired product were pooled and concentrated, yielding the slightly impure 2-tert-butyldimethylsiloxyl-9H-xanthene 4 (3.297 g, 79.5%) as an off-white solid: mp 67-69° C. 1H NMR (CDCl3): delta 7.12-7.19 (2H, m), 6.96-7.01 (2H, m), 6.89 (1H, d, J=8.5 Hz), 6.61-6.67 (2H, m), 3.98 (2H, s), 0.97 (9H, s) and 0.17 (6H, s); 1R (CHCl3): 2960, 2938, 1630, 1587, 1487, 1464, 1251, 1203, 1158, 1120, 976, 892, 868 and 843 cm-1.

Aufarbeitung

  1. customquenched with saturated NaHCO3 solution
  2. extractionThe aqueous layer was extracted two times with 10% EtOAc-hexanes
  3. washThe combined organic layers were washed with water
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. washeluted with hexanes
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-c386e0a451d44d56bfdccef4cc2427a2
Quelldatensatz
uspto-grants-2000_12
Patentnummer
US06162610

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