Nitrogen → 4-(((tert-Butyldimethylsilyl)oxy)methyl)-2-(2-methoxypropan-2-yl)oxazole

HRID 82821Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 82821
N#N.[Si:3]([O:10][CH2:11][C:12]1[N:13]=[C:14]([C:17]([OH:20])([CH3:19])[CH3:18])[O:15][CH:16]=1)([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4].[CH3:21]I>C(Cl)Cl>[Si:3]([O:10][CH2:11][C:12]1[N:13]=[C:14]([C:17]([O:20][CH3:21])([CH3:19])[CH3:18])[O:15][CH:16]=1)([C:6]([CH3:9])([CH3:7])[CH3:8])([CH3:5])[CH3:4]

Komponenten

5

Edukt 3

HCID 947NitrogenHCID 6328Methyl iodideHCID 866982042-(4-(((tert-Butyldimethylsilyl)oxy)methyl)oxazol-2-yl)propan-2-ol

Produkt 1

HCID 866982054-(((tert-Butyldimethylsilyl)oxy)methyl)-2-(2-methoxypropan-2-yl)oxazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 2-(4-(((tert-butyldimethylsilyl)oxy)methyl)oxazol-2-yl)propan-2-ol (153 mg, 0.56 mmol) in CH2Cl2 (0.4 mL) was treated with MeI (0.08 mL, 1.35 mmol) followed by Ag2O (196 mg, 0.85 mmol). The resulting mixture (protected form light) was stirred overnight at 40° C. The reaction mixture was filtered and the solvent was removed under reduced pressure. Purification of the residue by FC (7:3 hept-EA) gave the title compound as an orange oil. TLC: rf (7:3 hept-EA)=0.40. LC-MS-conditions 07: tR=0.99 min, [M+H]+=286.20.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent was removed under reduced pressure
  3. customPurification of the residue by FC (7:3 hept-EA)

Quellen und Nachweise

ORD-Eintrag
ord-63f0668deede40afaa680b78eb078207
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846733B2

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