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

HRID 76860Notes

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-2].[O-2].[Mn+4]>[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

Conditions

Temperature: 90 °C

Procedure

To 1-(1-trityl-1H-imidazol-4-yl)ethanol (8.06 g, 22.7 mmol) in dioxane (400 mL) is added manganese dioxide (9.9 g, 113.8 mmol). The reaction mixture is heated to 90° C. and stirred for 18 h. The reaction is allowed to cool to room temperature and filtered through diatomaceous earth. The filtered solvent is removed in vacuo to yield the product. MS (ESI) m/z 353 (M+H) (prepared similarly in Bioorg. Med. Chem. 2004, 12(9), 2251.)

Workup

temperatureto cool to room temperature
filtrationfiltered through diatomaceous earth
customThe filtered solvent is removed in vacuo
customto yield the product
customMS (ESI) m/z 353 (M+H) (prepared similarly in Bioorg

Sources & evidence

ORD record: ord-0af50c8551d04d8bb995693e48cbf8f2
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835646B2

Reaction notes

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