Carbon Tetrachloride → HCID 86592539, compound

HRID 1374451Notes

Reaction equation

HRID 1374451 reaction equation
O[CH2:2][C@@H:3]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH2:5][N:4]1[C:12]([O:14][CH2:15][CH:16]=[CH2:17])=[O:13].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:38]>C(Cl)(Cl)Cl>[Cl:38][CH2:2][C@@H:3]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH2:5][N:4]1[C:12]([O:14][CH2:15][CH:16]=[CH2:17])=[O:13]

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 131726205HCID 131726205, compound

Product 1

HCID 86592539HCID 86592539, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 1-allyl 3-methyl(2S)-2-(hydroxymethyl)-2,5-dihydro-1H-pyrrole-1,3-dicarboxylate (1.29 g, 4.28 mmol) in carbontetrachloride (16 ml) was added at room temperature triphenylphosphine (1.35 g) and the mixture was refluxed under heating for 6 hours. The insoluble materials were dissolved in chloroform and the solvent was removed in vacuo. The residue was purified with silica gel (150 g) column chromatography (hexane/ethyl acetate 4/1→2/1) to give 1-allyl 3-methyl (2S)-2-(chloromethyl)-2,5-dihydro-1H-pyrrole-1,3-dicarboxylate (268 mg, 24%).

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 6 hours
  3. customthe solvent was removed in vacuo
  4. customThe residue was purified with silica gel (150 g) column chromatography (hexane/ethyl acetate 4/1→2/1)

Sources & evidence

ORD record
ord-9c3159b8f2804600a4c190482a009ccf
Source dataset
uspto-grants-2007_01
Patent number
US07163936B2

Reaction notes

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