Triethylamine → Methanesulfonic acid [(R)-2,2-dimethyl-[1,3]dioxolan-4-yl]methyl ester

HRID 2222976Notes

Reaction equation

HRID 2222976 reaction equation
[CH3:1][C:2]1([CH3:9])[O:6][C@@H:5]([CH2:7][OH:8])[CH2:4][O:3]1.C(N(CC)CC)C.[CH3:17][S:18](Cl)(=[O:20])=[O:19]>ClCCl.O>[CH3:1][C:2]1([CH3:9])[O:6][C@@H:5]([CH2:7][O:8][S:18]([CH3:17])(=[O:20])=[O:19])[CH2:4][O:3]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 736057(+)-Solketal

Product 1

HCID 15570842Methanesulfonic acid [(R)-2,2-dimethyl-[1,3]dioxolan-4-yl]methyl esterYield 100.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-methanol (2.0 g, 15.13 mmol) and triethylamine (2.53 ml, 18.16 mmol) were dissolved in dichloromethane (60 mL) followed by the addition of methanesulfonyl chloride (1.35 ml, 17.40 mmol) at 0° C. The reaction was warmed to ambinet temperature, stirred overnight, and then diluted with water. The organic layer was washed with saturated aqueous sodium bicarbonate solution, brine and dried over sodium sulfate. Removal of solvents gave methanesulfonic acid (R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester as an oil (3.2 g, 100%).

Workup

  1. temperatureThe reaction was warmed
  2. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution, brine
  3. dry with materialdried over sodium sulfate
  4. customRemoval of solvents

Sources & evidence

ORD record
ord-a2f1e33c44a844fdb39cf8ae492ee052
Source dataset
uspto-grants-2008_05
Patent number
US07371869B2

Reaction notes

Loading…