Imidazole → HCID 10991787, Verbindung

HRID 718013Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 718013
N1C=CN=C1.[Si:6](Cl)([C:19]([CH3:22])([CH3:21])[CH3:20])([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[OH:24][CH2:25][C@H:26]1[O:30][C:29](=[O:31])[CH:28]=[CH:27]1>CN(C)C=O>[Si:6]([O:24][CH2:25][C@H:26]1[O:30][C:29](=[O:31])[CH:28]=[CH:27]1)([C:19]([CH3:22])([CH3:21])[CH3:20])([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Komponenten

5

Edukt 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 10176122(S)-(-)-5-Hydroxymethyl-2(5H)-furanone

Produkt 1

HCID 10991787HCID 10991787, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Imidazole (1.22 g, 17.6 mmol) and tert-butyl(diphenyl)silyl chloride (3.95 mL, 15.4 mmol) were added to a solution of (5S)-5-(hydroxymethyl)furan-2(5H)-one (1.60 g, 14.0 mmol) in N,N-dimethylformamide (50 mL), and the reaction mixture was stirred at room temperature for 18 hours. It was then partitioned between tert-butyl methyl ether and water; the organic layer was washed twice with water, dried over magnesium sulfate, filtered, and concentrated in vacuo. Silica gel chromatography (Gradient: 5% to 30% ethyl acetate in heptane) afforded the product as a white solid. Yield: 5.20 g, quantitative. 1H NMR (400 MHz, CDCl3) δ 7.63-7.66 (m, 4H), 7.38-7.49 (m, 7H), 6.19 (dd, J=5.7, 2.0 Hz, 1H), 5.06-5.10 (m, 1H), 3.93 (dd, half of ABX pattern, J=10.9, 4.5 Hz, 1H), 3.88 (dd, half of ABX pattern, J=10.8, 5.0 Hz, 1H), 1.05 (s, 9H).

Aufarbeitung

  1. customIt was then partitioned between tert-butyl methyl ether and water
  2. washthe organic layer was washed twice with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5549bbf65e7d49e89e2980461b3544b9
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09193726B2

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