Methanesulfonyl chloride → 2-(6-Methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl methanesulfonate

HRID 1502038Notes

Reaction equation

HRID 1502038 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[C:13]([CH3:14])=[CH:12][C:7]2[C:8](=[O:11])[O:9][CH2:10][C:6]=2[CH:5]=1.[CH3:15][S:16](Cl)(=[O:18])=[O:17]>C(Cl)Cl>[CH3:15][S:16]([O:1][CH2:2][CH2:3][C:4]1[C:13]([CH3:14])=[CH:12][C:7]2[C:8](=[O:11])[O:9][CH2:10][C:6]=2[CH:5]=1)(=[O:18])=[O:17]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 666440355-(2-hydroxyethyl)-6-methyl-2-benzofuran-1(3H)-one

Product 1

HCID 866472962-(6-Methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(2-hydroxyethyl)-6-methyl-2-benzofuran-1(3H)-one (1.20 g, 6.25 mmol) and TEA (2.5 g, 25 mmol) in DCM (100 mL) was added MsCl (1.40 g, 12.5 mmol) at 0° C. The mixture was stirred at ambient temperature overnight, then was washed with water and brine. The organic layer was dried and concentrated to dryness. The resulting 2-(6-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl methanesulfonate was used for the next step without any purification.

Workup

  1. washwas washed with water and brine
  2. customThe organic layer was dried
  3. concentrationconcentrated to dryness
  4. customThe resulting 2-(6-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl methanesulfonate was used for the next step without any purification

Sources & evidence

ORD record
ord-2bb604d3425549f78acd49ece1c56620
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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