Pyridine, hydrofluoride (1:1) → 4-(2-Fluoro-1,2-dimethylpropyl)-2-methyl-1-trityl-1h-imidazole

HRID 216322

Reaktionsgleichung

Reaktionsgleichung von HRID 216322
[CH3:1][C:2](C)([CH3:30])[CH:3]([C:5]1[N:6]=[C:7]([CH3:29])[N:8]([C:10]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:9]=1)O.[CH:32]1C=CN=CC=1.[FH:38].[Si](C(O)C)(C)(C)C>C(Cl)Cl>[F:38][C:2]([CH3:1])([CH3:30])[CH:3]([C:5]1[N:6]=[C:7]([CH3:29])[N:8]([C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:9]=1)[CH3:32]

Komponenten

5

Edukt 3

HCID 64774Pyridine, hydrofluoride (1:1)HCID 124478981-(Trimethylsilyl)ethanolHCID 686681432,2-dimethyl-1-(2-methyl-1-trityl-1H-imidazol-4-yl)propan-1-ol

Produkt 1

HCID 591619854-(2-Fluoro-1,2-dimethylpropyl)-2-methyl-1-trityl-1h-imidazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2,2-Dimethyl-1-(2-methyl-1-trityl-1H-imidazol-4-yl)propan-1-ol (200 mg, 0.49 mmol) in a minimal volume of methylene chloride was added to HF-pyridine (2 mL) at 0° C. After stirring at ambient temperature overnight, the reaction was added dropwise to TMS-ethanol and partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. Organic phase was washed with brine, dried (sodium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 10-70% ethyl acetate/hexane afforded the title compound.

Aufarbeitung

  1. custompartitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  2. washOrganic phase was washed with brine
  3. dry with materialdried (sodium sulfate)
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b7aae145552f46dca8e008e9f0d81512
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193228B2

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