3-Chlorophenol → HCID 22857697, compound

HRID 2259202Notes

Reaction equation

HRID 2259202 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[CH2:7][OH:8].[Cl:9][C:10]1[CH:11]=[C:12](O)[CH:13]=[CH:14][CH:15]=1>C1COCC1>[Cl:9][C:10]1[CH:15]=[C:14]([CH:13]=[CH:12][CH:11]=1)[O:8][CH2:7][C@@H:3]1[CH2:4][CH2:5][CH2:6][N:2]1[CH3:1]

Participants

4

Reactant 2

HCID 79333-ChlorophenolHCID 643492(2S)-1-Methyl-2-pyrrolidinemethanol

Product 1

HCID 22857697HCID 22857697, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 2 g (17.4 mmol) sample of (S)-1-methyl-2-pyrrolidinemethanol (from Aldrich) and 2.8 g (22 mmol) of 3-chlorophenol (Aldrich) were added to a complex of TPP and TBAD, (prepared as in Example 5b above, 22 mmol of each) in 150 mL of THF. The reaction was stirred for 4 hr. The solvents were removed, the residue was stirred with 15% HCl, and the mixture was extracted with ether. The aqueous solution was then adjusted to pH 12 with K2CO3 and extracted with methylene chloride. The solvent was removed, and the residue was triturated with ether, the precipitate was removed by filtration, and the solvent was removed to give the crude product. The residue was purified by chromatography on silica gel.

Workup

  1. customThe solvents were removed
  2. stirringthe residue was stirred with 15% HCl
  3. extractionthe mixture was extracted with ether
  4. extractionextracted with methylene chloride
  5. customThe solvent was removed
  6. customthe residue was triturated with ether
  7. customthe precipitate was removed by filtration
  8. customthe solvent was removed

Sources & evidence

ORD record
ord-edaaede24386468892e4007b6ce58fa4
Source dataset
uspto-grants-1995_12
Patent number
US05472958

Reaction notes

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