1-(1-trityl-1H-imidazol-4-yl)ethanol → 1-(1-trityl-1H-imidazol-4-yl)ethanone

HRID 2074109Notes

Reaction equation

HRID 2074109 reaction equation
[C:1]([N:20]1[CH:24]=[C:23]([CH:25]([OH:27])[CH3:26])[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>O1CCOCC1.O=[Mn]=O>[C:1]([N:20]1[CH:24]=[C:23]([C:25](=[O:27])[CH3:26])[N:22]=[CH:21]1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 123447941-(1-trityl-1H-imidazol-4-yl)ethanol

Product 1

HCID 104280901-(1-trityl-1H-imidazol-4-yl)ethanoneYield 100.4%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 1-(1-trityl-1H-imidazol-4-yl)ethanol (4.0 g, 11.3 mmol) in anhydrous 1,4-dioxane (150 mL) was added activated MnO2 (2.5 g, 28.2 mmol) at 0° C. The mixture was refluxed for 2 hours. TLC (EtOAc/Petroleum ether 1:2) showed the starting material was consumed completely, and the mixture was filtered. The filter cake was washed with dry CH2Cl2 (5×50 mL) and the filtrate was evaporated to afford the title compound (4.0 g, 100%) as a white solid.

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. customwas consumed completely
  3. filtrationthe mixture was filtered
  4. washThe filter cake was washed with dry CH2Cl2 (5×50 mL)
  5. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-b6222423c6fe42c1ac54d1d9d01966a5
Source dataset
uspto-grants-2011_04
Patent number
US07919488B2

Reaction notes

Loading…