Triethylamine → Cyclopentylmethyl methanesulfonate

HRID 1032895Notes

Reaction equation

HRID 1032895 reaction equation
[CH:1]1([CH2:6][OH:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:8][S:9](Cl)(=[O:11])=[O:10].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH3:8][S:9]([O:7][CH2:6][CH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)(=[O:11])=[O:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 77195Cyclopentanemethanol

Product 1

HCID 15712513Cyclopentylmethyl methanesulfonateYield 100%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
4 °C

Procedure

Cyclopentanemethanol (50.0 g; 0.484 mol) and methane-sulfonyl chloride (67.0 g; 0.581 mol) in toluene (500 ml) were stirred and cooled to 4° C. Triethylamine (68.0 g; 0.678 mol) was added dropwise with external cooling so that the reaction temperature remained below 20° C. The reaction mixture is stirred under dry nitrogen at room temperature overnight. The reaction mixture was quenched with water (500 ml) and ether (500 ml), the organic phase separated, washed with water (500 ml) and saturated brine (500 ml) and dried (MgSO4). The solution is filtered and the solvent evaporated, to afford cyclopentylmethyl methanesulfonate (86.0 g; 100% yield) as a colorless liquid. NMR - d(CDCl3 ; 60 MHz) 0.8-2.6 (9H, m), 3.1 (3H, s) and 4.15 (2H, d, J=8 Hz).

Workup

  1. temperaturewith external cooling so that the reaction temperature
  2. customremained below 20° C
  3. customThe reaction mixture was quenched with water (500 ml) and ether (500 ml)
  4. customthe organic phase separated
  5. washwashed with water (500 ml) and saturated brine (500 ml)
  6. dry with materialdried (MgSO4)
  7. filtrationThe solution is filtered
  8. customthe solvent evaporated

Sources & evidence

ORD record
ord-3f779ab9c8ec444f81083bb9ee7a3072
Source dataset
uspto-grants-1994_05
Patent number
US05308830

Reaction notes

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