1-(1-Trityl-1H-imidazol-4-yl)propane-1,3-diol → 3-Hydroxy-1-(1-trityl-1H-imidazol-4-YL)propan-1-one

HRID 724207Notes

Reaction equation

HRID 724207 reaction equation
[C:1]([N:20]1[CH:24]=[C:23]([CH:25]([OH:29])[CH2:26][CH2:27][OH:28])[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>ClCCl.[O-2].[O-2].[Mn+4]>[OH:28][CH2:27][CH2:26][C:25]([C:23]1[N:22]=[CH:21][N:20]([C:1]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=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]

Participants

4

Reactant 1

HCID 218796071-(1-Trityl-1H-imidazol-4-yl)propane-1,3-diol

Product 1

HCID 218796303-Hydroxy-1-(1-trityl-1H-imidazol-4-YL)propan-1-oneYield 95.6%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

1-(1-Trityl-1H-imidazol-4-yl)-1,3-propanediol (135.9 g) was dissolved in dichloromethane (1.76 L) and manganese dioxide (262 g) was added, which was followed by vigorous stirring at room temperature for 66 h. An insoluble material was filtered off by celite filtration and the filtrate was concentrated to dryness. The residue was suspended in ethyl acetate (1.5 L) and an aqueous solution (1 M; 3.5 L) of Rochelle salt was added, which was followed by stirring with a mechanical stirrer for 3 days. The reaction mixture was partitioned, and the organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The aqueous layer was extracted again with ethyl acetate and treated in the same manner. The organic layer was combined and the solvent was evaporated to give the title compound (129.3 g) as a pale-brown caramel.

Workup

  1. filtrationAn insoluble material was filtered off by celite filtration
  2. concentrationthe filtrate was concentrated to dryness
  3. additionan aqueous solution (1 M; 3.5 L) of Rochelle salt was added
  4. stirringby stirring with a mechanical stirrer for 3 days
  5. customThe reaction mixture was partitioned
  6. washthe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. extractionThe aqueous layer was extracted again with ethyl acetate
  9. additiontreated in the same manner
  10. customthe solvent was evaporated

Sources & evidence

ORD record
ord-21c82cd1b18945cbade7834660e31f83
Source dataset
uspto-grants-2006_11
Patent number
US07141598B2

Reaction notes

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