Trityl chloride → HCID 15372343, compound

HRID 80302Notes

Reaction equation

HRID 80302 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:6]1([C:12]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)Cl)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])O.[Na+]>C(OCC)(=O)C.C(#N)C>[C:6]1([C:12]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

7

Reactant 4

HCID 6456Trityl chlorideHCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 516892Sodium Bicarbonate

Product 1

HCID 15372343HCID 15372343, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

Pyrrolidine (0.26 g, 3.66 mmol) (Wako Pure Chemical Industries, Ltd.), triphenylchloromethane (1.02 g, 3.66 mmol) (Wako Pure Chemical Industries, Ltd.), and potassium carbonate (0.51 g, 3.66 mmol) (Wako Pure Chemical Industries, Ltd.) were added to acetonitrile (30 mL) (Wako Pure Chemical Industries, Ltd.), and the mixture was refluxed for 5 hours. A saturated aqueous solution of sodium hydrogen carbonate (Wako Pure Chemical Industries, Ltd.) was added to the reaction solution, and mixture was extracted with ethyl acetate (Wako Pure Chemical Industries, Ltd.). The organic layer was dried with anhydrous sodium sulfate (Wako Pure Chemical Industries, Ltd.), and the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography (n-hexane (Wako Pure Chemical Industries, Ltd.):ethyl acetate (Wako Pure Chemical Industries, Ltd.)=9:1 as an eluent)), to thereby obtain the title compound (0.45 g, 80% yield).

Workup

  1. temperaturethe mixture was refluxed for 5 hours
  2. extractionwas extracted with ethyl acetate (Wako Pure Chemical Industries, Ltd.)
  3. dry with materialThe organic layer was dried with anhydrous sodium sulfate (Wako Pure Chemical Industries, Ltd.)
  4. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-4f9e20a52a404ed7bbb0f363dfb9f8be
Source dataset
uspto-grants-2014_09
Patent number
US08846012B2

Reaction notes

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