Methanesulfonyl chloride → HCID 58591583, compound

HRID 746600Notes

Reaction equation

HRID 746600 reaction equation
[S:1]1[C:5]([CH2:6][CH2:7][OH:8])=[CH:4][C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]1=2.CCN(C(C)C)C(C)C.[S:22](Cl)([CH3:25])(=[O:24])=[O:23]>C(Cl)Cl>[S:1]1[C:5]([CH2:6][CH2:7][O:8][S:22]([CH3:25])(=[O:24])=[O:23])=[CH:4][C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]1=2

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 280609Benzo(b)thiophene-2-ethanol

Product 1

HCID 58591583HCID 58591583, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-benzo[b]thiophen-2-yl-ethanol (16.8 mmol) in CH2Cl2 (60 mL) were added DIPEA (33.6 mmol) and mesylchloride (20.2 mmol.) The mixture was stirred for 18 hrs at RT, diluted with CH2Cl2, washed with sat. NaHCO3 (3×), brine (1×), dried (MgSO4) and concentrated in vacuo to give 4.3 g (99%) of methanesulfonic acid 2-benzo[b]thiophen-2-yl-ethyl ester which was used in the next step without further purification.

Workup

  1. washwashed with sat. NaHCO3 (3×), brine (1×)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-77cb905d7f5a41b199e7785654f7949e
Source dataset
uspto-grants-2008_07
Patent number
US07393865B2

Reaction notes

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