Trityl chloride → HCID 21879616, compound

HRID 724217Notes

Reaction equation

HRID 724217 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]([C:7]1[N:8]=[CH:9][NH:10][CH:11]=1)=[O:6].C(N(CC)CC)C.Cl[C:20]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C=O)C.[Cl-].[Na+].O>[OH:1][CH2:2][CH2:3][CH2:4][C:5]([C:7]1[N:8]=[CH:9][N:10]([C:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:11]=1)=[O:6]

Participants

6

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 178520679HCID 178520679, compound

Product 1

HCID 21879616HCID 21879616, compoundYield 106.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

4-Hydroxy-1-(1H-imidazol-4-yl)butan-1-one (9.23 g) was dissolved in N,N′-dimethylformamide (120 ml), and triethylamine (12.5 ml) and chlorotriphenylmethane (16.69 g) were added. The mixture was stirred at room temperature for 2 h. Brine was added and the mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent; ethyl acetate:hexane=9:1) to give the title compound (25.22 g) as an orange oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (eluent; ethyl acetate:hexane=9:1)

Sources & evidence

ORD record
ord-9158cc5455864e2eb833bb11c0c05309
Source dataset
uspto-grants-2006_11
Patent number
US07141598B2

Reaction notes

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