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

HRID 1186951Notes

Reaction equation

HRID 1186951 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 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 collected 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-e46f5db4486943da982c5cb4dc184520
Source dataset
uspto-grants-2014_03
Patent number
US08673920B2

Reaction notes

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