Imidazole → HCID 18618529, Verbindung

HRID 1264181Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1264181
[F:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][CH2:7][C@@H:8]2[CH2:12][CH2:11][CH:10]([OH:13])[O:9]2)=[CH:4][CH:3]=1.N1C=CN=C1.[Si:21](Cl)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22]>C(Cl)Cl>[F:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][CH2:7][CH:8]2[CH2:12][CH2:11][CH:10]([O:13][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])[O:9]2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 10822410(2S)-(4-fluorophenoxymethyl)-5-hydroxytetrahydrofuran

Produkt 1

HCID 18618529HCID 18618529, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of 3.47 g of (2S)-(4-fluorophenoxymethyl)-5-hydroxytetrahydrofuran 7 in 30 mL of CH2Cl2 was taken in an 100 mL round bottom flask equipped with a magnetic stir bar and nitrogen inlet. That solution was cooled in an ice-water bath and 2.18 g (0.032 mol) of imidazole was added, followed by a solution of 3.6 g (0.024 mol) of tert-butyldimethylsilylchloride (TBDMSCl) in 30 mL of CH2Cl2. The reaction mixture then was stirred at room temperature for 3 hours, and the reaction then quenched with ice water, the organic layer separated, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography using light petroleum ether:ethyl acetate (9:1) to yield (2S) (4-fluorophenoxymethyl)-5-(tert-butyldimethylsiloxy)-tetrahydrofuran) 8 as an oil (5.1 g, 95%). 1H NMR (200 MHz, CDCl3): δ0.09 (s, 6H), 0.88 (s, 9H), 1.72-2.34 (m, 4H), 3.76=4.08 (m, 2H), 4.28-4.54 (m, 1H), 5.47. (s, 1/3H), 5.54 (d, J=4.5 Hz, 2/3H), 6.75-7.0 (m, 4H).

Aufarbeitung

  1. customequipped with a magnetic stir bar and nitrogen inlet
  2. temperatureThat solution was cooled in an ice-water bath
  3. customthe reaction
  4. customthen quenched with ice water
  5. customthe organic layer separated
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-fe17cd10660747f3bc2b2c4ebd1f1eb4
Quelldatensatz
uspto-grants-2003_04
Patentnummer
US06541647B2

Notizen zur Reaktion

Wird geladen…