Ethyl Acetate → 2-(Methylsulfonyl)ethyl methanesulfonate

HRID 1445229Notes

Reaction equation

HRID 1445229 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH3:6][S:7]([CH2:10][CH2:11][OH:12])(=[O:9])=[O:8].CCN(C(C)C)C(C)C.CCOC(C)=O>C(Cl)Cl>[CH3:6][S:7]([CH2:10][CH2:11][O:12][S:2]([CH3:1])(=[O:4])=[O:3])(=[O:9])=[O:8]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 848342-(Methylsulfonyl)ethanol

Product 1

HCID 184645972-(Methylsulfonyl)ethyl methanesulfonateYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of methanesulfonyl chloride (484 mg, 4.23 mmol) in 15 mL of DCM at 0° C. was added 2-methanesulfonyl-ethanol (500 mg, 4.03 mmol) in 10 mL of DCM followed by DIEA (1.05 mL, 6.05 mmol) under Ar. The mixture was warmed to RT and stirred for 20 h under Ar. The mixture was treated with 100 mL of EtOAc and washed with H2O (3×20 mL), brine (20 mL) and dried (Na2SO4). Removal of the solvent in vacuo gave 534 mg (66%) of the title compound as a brown oil. 1H-NMR (CDCl3; 400 MHz): δ 4.67 (d, 2H, J=5.5 Hz), 3.46 (d, 2H, J=5.5 Hz), 3.11 (s, 3H), 3.04 (s, 3H).

Workup

  1. washwashed with H2O (3×20 mL), brine (20 mL)
  2. dry with materialdried (Na2SO4)
  3. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-edd1d2ad659249108a87dba36a1646e5
Source dataset
uspto-grants-2010_02
Patent number
US07662837B2

Reaction notes

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