Dichloromethane → 1-methyl-1H-pyrrole-2-ethanol methanesulfonate

HRID 2210803Notes

Reaction equation

HRID 2210803 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH2:7][CH2:8][OH:9].C(N(CC)CC)C.ClCCl.[CH3:20][S:21](Cl)(=[O:23])=[O:22]>O>[CH3:20][S:21]([O:9][CH2:8][CH2:7][C:3]1[N:2]([CH3:1])[CH:6]=[CH:5][CH:4]=1)(=[O:23])=[O:22]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 117685722-(1-methyl-1H-pyrrol-2-yl)ethan-1-ol

Product 1

HCID 217469581-methyl-1H-pyrrole-2-ethanol methanesulfonateYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred and cooled (ice-bath) mixture of 49 g of 1-methyl-1H-pyrrole-2-ethanol, 47.6 g of N,N-diethylethanamine and 500 ml of dichloromethane, there were added portionwise 34 ml of methanesulfonyl chloride. Stirring was continued overnight at room temperature. The reaction mixture was diluted with water and the product was extracted with dichloromethane. The extract was dried, filtered and evaporated, yielding 85.5 g (100%)of 1-methyl-1H-pyrrole-2-ethanol methanesulfonate (ester) (interm. 3);

Workup

  1. temperaturecooled
  2. stirringStirring
  3. extractionthe product was extracted with dichloromethane
  4. customThe extract was dried
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-c968bd80c9a54fc5b467baf6eb72a133
Source dataset
uspto-grants-1995_10
Patent number
US05461050

Reaction notes

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