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

HRID 1848419Notes

Reaction equation

HRID 1848419 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 collected title compound 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 collected title compound
  5. customwas used for the next step without any purification

Sources & evidence

ORD record
ord-3c5d90d714b7438386dc649d68eafee7
Source dataset
uspto-grants-2015_02
Patent number
US08952166B2

Reaction notes

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