Methanesulfonyl chloride → HCID 86602659, compound

HRID 746604Notes

Reaction equation

HRID 746604 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:9]=[C:8]([CH2:10][CH2:11][OH:12])[S:7][C:6]=2[CH:13]=1.[CH3:14][S:15](Cl)(=[O:17])=[O:16].CCN(C(C)C)C(C)C>ClCCl>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:9]=[C:8]([CH2:10][CH2:11][O:12][S:15]([CH3:14])(=[O:17])=[O:16])[S:7][C:6]=2[CH:13]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 58591564HCID 58591564, compound

Product 1

HCID 86602659HCID 86602659, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.) solution of 2-(6-methyl-benzo[b]thiophen-2-yl)-ethanol (3.22 g, 16.8) mmol) in dichloromethane (100 mL), methanesulfonylchloride (1.56 mL, 20.1 mmol) and DIEA (5.96 mL, 33.5 mmol) were added. The mixture was stirred for 15 min at 0° C. and then allowed to reach room temperature and stirred for an additional 2.5 hrs. It was washed with sat. NaHCO3 (2×) and brine (1×), dried (Na2SO4), filtered and concentrated in vacuo. Methanesulfonic acid 2-(6-methyl-benzo[b]thiophen-2-yl)-ethyl ester was obtained as a solid and used without further purification.

Workup

  1. customto reach room temperature
  2. stirringstirred for an additional 2.5 hrs
  3. washIt was washed with sat. NaHCO3 (2×) and brine (1×)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1ccd6ca2908c48ecaba5009e727bd98f
Source dataset
uspto-grants-2008_07
Patent number
US07393865B2

Reaction notes

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