Water → 3-(Methylsulfonyl)propyl methanesulfonate

HRID 417338Notes

Reaction equation

HRID 417338 reaction equation
[CH3:1][S:2]([CH2:5][CH2:6][CH2:7][OH:8])(=[O:4])=[O:3].C(N(CC)CC)C.[CH3:16][S:17](Cl)(=[O:19])=[O:18].O>ClCCl>[CH3:1][S:2]([CH2:5][CH2:6][CH2:7][O:8][S:17]([CH3:16])(=[O:19])=[O:18])(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 2004243-(Methylsulfonyl)-1-propanol

Product 1

HCID 102627583-(Methylsulfonyl)propyl methanesulfonateYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Step A To a solution of 3-methanesulfonyl-propan-1-ol (Cambridge) (0.5 g, 3.6 mmol) in dichloromethane (3 mL) at 0° C. was added triethylamine (0.5 g, 5 mmol), and methanesulfonyl chloride (0.3 mL, 4 mmol, Aldrich). The reaction mixture was stirred at 0° C. for 2 h. The mixture was poured into water, extracted with dichloromethane. The organic layer was separated, washed with water, brine, dried over MgSO4, and concentrated to give crude methanesulfonic acid 3-methanesulfonyl-propyl ester as a yellow oil (Yield 0.7 g, 90%).

Workup

  1. extractionextracted with dichloromethane
  2. customThe organic layer was separated
  3. washwashed with water, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f0bbd623ad704d3fb4e1c7c6bfa3c612
Source dataset
uspto-grants-2012_01
Patent number
US08088815B2

Reaction notes

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