Triethylamine → Methanesulphonic acid 2-(6-methoxyindan-1-yl)ethyl ester

HRID 1762585Notes

Reaction equation

HRID 1762585 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][CH:9]2[CH2:12][CH2:13][OH:14])=[CH:5][CH:4]=1.[CH3:15][S:16](Cl)(=[O:18])=[O:17].C(N(CC)CC)C>ClCCl>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][CH:9]2[CH2:12][CH2:13][O:14][S:16]([CH3:15])(=[O:18])=[O:17])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 109978572-(6-Methoxyindan-1-yl)ethanol

Product 1

HCID 53897303Methanesulphonic acid 2-(6-methoxyindan-1-yl)ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5.0 g (26.0 mmol) of crude 2-(6-methoxyindan-1-yl)ethanol are dissolved in 50 ml of dichloromethane and, while cooling with ice, 3.6 g (31 mmol) of methanesulphonic acid chloride and 3.1 g (31 mmol) of triethylamine are added dropwise. The mixture is stirred at room temperature for 3 hours, the triethylammonium chloride which has precipitated is filtered off and the filtrate is extracted by shaking with ice-water. The organic phases are washed with saturated sodium chloride solution, dried over magnesium sulphate and concentrated by evaporation at 40° under reduced pressure. Methanesulphonic acid 2-(6-methoxyindan-1-yl)ethyl ester is obtained which can be used without further purification.

Workup

  1. additionare added dropwise
  2. customthe triethylammonium chloride which has precipitated
  3. filtrationis filtered off
  4. extractionthe filtrate is extracted
  5. stirringby shaking with ice-water
  6. washThe organic phases are washed with saturated sodium chloride solution
  7. dry with materialdried over magnesium sulphate
  8. concentrationconcentrated by evaporation at 40° under reduced pressure

Sources & evidence

ORD record
ord-5b94a7c5ec374035b1be7a9f5adcf065
Source dataset
uspto-grants-1989_05
Patent number
US04833169

Reaction notes

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