Triethylamine → 3-(1-Pyrrolyl)benzyl methanesulfonate

HRID 2254442Notes

Reaction equation

HRID 2254442 reaction equation
[N:1]1([C:6]2[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=2)[CH2:9][OH:10])[CH:5]=[CH:4][CH:3]=[CH:2]1.[CH3:14][S:15](Cl)(=[O:17])=[O:16].C(N(CC)CC)C>C(Cl)Cl>[CH3:14][S:15]([O:10][CH2:9][C:8]1[CH:11]=[CH:12][CH:13]=[C:6]([N:1]2[CH:5]=[CH:4][CH:3]=[CH:2]2)[CH:7]=1)(=[O:17])=[O:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 2776531[3-(1H-Pyrrol-1-yl)phenyl]methanol

Product 1

HCID 197445313-(1-Pyrrolyl)benzyl methanesulfonateYield 93.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

170 mg of the resulting alcohol compound was dissolved in 10 ml of methylene chloride, and 120 mg of methanesulfonyl chloride and 150 mg of triethylamine were added. The mixture was stirred for 1 hour under ice cooling. The reaction mixture was washed with water, and dried over anhydrous magnesium sulfate. The solvent was evaporated to give 230 mg (yield 92%) of the captioned compound as a pale yellow oil.

Workup

  1. washThe reaction mixture was washed with water
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated

Sources & evidence

ORD record
ord-df63b00ecffe444bbbaf046c5204bea7
Source dataset
uspto-grants-1993_08
Patent number
US05234946

Reaction notes

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