Acetic Anhydride → (1-Trityl-1H-imidazol-4-YL)methyl acetate

HRID 15413

Reaktionsgleichung

Reaktionsgleichung von HRID 15413
[C:1]([N:20]1[CH:24]=[C:23]([CH2:25][OH:26])[N:22]=[CH:21]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:27](OC(=O)C)(=[O:29])[CH3:28].CCOC(C)=O>N1C=CC=CC=1>[C:27]([O:26][CH2:25][C:23]1[N:22]=[CH:21][N:20]([C:1]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:24]=1)(=[O:29])[CH3:28]

Komponenten

5

Edukt 3

HCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 382182[1-(triphenylmethyl)-1H-imidazol-4-yl]methanol

Produkt 1

HCID 10762461(1-Trityl-1H-imidazol-4-YL)methyl acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a suspension of the title A compound 1-trityl-4-hydroxymethyl-1H-imidazole (34.5 g, 101 mmol) in pyridine (200 mL) is added acetic anhydride (28.6 mL, 303 mmol) in a dropwise fashion and the reaction is stirred until it becomes clear. The reaction mixture is poured into EtOAc and then washed with 0.5N aqueous HCl, saturated aqueous sodium bicarbonate and brine. The combined organic phases are dried over anhydrous sodium sulfate and then filtered through a silica pad yielding a solid after removal of the solvent in vacuo. The solid is triturated with diethyl ether to give 4-acetoxymethyl-1-tritylimidazole: m.p. 133-134° C.; 1H-NMR (DMSO-d6) δ 7.42 (10H, m), 7.09 (6H, m), 6.99 (1H, s), 4.89 (2H, s), 1.99 (3H, s); e/z (ES) 383 (M+1, 5%), 243 (100%).

Aufarbeitung

  1. washwashed with 0.5N aqueous HCl, saturated aqueous sodium bicarbonate and brine
  2. dry with materialThe combined organic phases are dried over anhydrous sodium sulfate
  3. filtrationfiltered through a silica pad
  4. customyielding a solid
  5. customafter removal of the solvent in vacuo
  6. customThe solid is triturated with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-e1e02d6c5b8641a7ae057333c534d7f7
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732603B2

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