Imidazole → 4-(1-((tert-butyldiphenylsilyl)oxy)ethyl)-1H-1,2,3-triazole

HRID 708521Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 708521
[NH:1]1[CH:5]=[C:4]([CH:6]([OH:8])[CH3:7])[N:3]=[N:2]1.N1C=CN=C1.[CH3:14][C:15]([Si:18](Cl)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([CH3:17])[CH3:16]>C(Cl)Cl>[Si:18]([O:8][CH:6]([C:4]1[N:3]=[N:2][NH:1][CH:5]=1)[CH3:7])([C:15]([CH3:17])([CH3:16])[CH3:14])([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

5

Edukt 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 178467229HCID 178467229, Verbindung

Produkt 1

HCID 1784771794-(1-((tert-butyldiphenylsilyl)oxy)ethyl)-1H-1,2,3-triazoleAusbeute 46,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 1-(1H-1,2,3-triazol-4-yl)ethanol (50.2 mmol) and imidazole (5.13 mg, 75 mmol) in DCM (50 ml) 0° C. was added TBDPSCl (14.6 mL, 55.2 mmol). After stirring at room temperature overnight the mixture was filtered through a celite pad and then concentrated to dryness. The resulting residue was dissolved in EtOAc, washed with water, brine, dried with sodium sulfate and concentrated. Purification of the crude residue via silica gel chromatography (EtOAc-Heptane, 5-25%) afforded the title compound (8.16 g, 46%) as a yellow oil. LCMS: Rt=1.09 min, m/z=352.1 (M+1) Method 2m_acidic. 1H NMR (400 MHz, CDCl3) δ ppm 7.71 (d, J=6.5 Hz, 2H) 7.64-7.54 (m, 3H) 7.49-7.28 (m, 6H) 5.14 (q, J=6.3 Hz, 1H) 1.46 (dd, J=6.3, 3.0 Hz, 3H) 1.08 (s, 9H).

Aufarbeitung

  1. filtrationwas filtered through a celite pad
  2. concentrationconcentrated to dryness
  3. dissolutionThe resulting residue was dissolved in EtOAc
  4. washwashed with water, brine
  5. dry with materialdried with sodium sulfate
  6. concentrationconcentrated
  7. customPurification of the crude residue via silica gel chromatography (EtOAc-Heptane, 5-25%)

Quellen und Nachweise

ORD-Eintrag
ord-be53d2d5d4404d9f920cbf93abf304b2
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09174978B2

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