Pyridine → 4-(6-(Methylsulfonyloxy)benzo(b)thiophen-2-yl)phenyl methanesulfonate

HRID 2198599Notes

Reaction equation

HRID 2198599 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:9]=[C:8]([C:10]3[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=3)[S:7][C:6]=2[CH:17]=1.N1C=CC=CC=1.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>CN(C)C1C=CN=CC=1.O>[CH3:24][S:25]([O:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:9]=[C:8]([C:10]3[CH:15]=[CH:14][C:13]([O:16][S:25]([CH3:24])(=[O:27])=[O:26])=[CH:12][CH:11]=3)[S:7][C:6]=2[CH:17]=1)(=[O:27])=[O:26]

Participants

6

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 4459202-(4-Hydroxyphenyl)benzo(b)thiophen-6-ol

Product 1

HCID 132860414-(6-(Methylsulfonyloxy)benzo(b)thiophen-2-yl)phenyl methanesulfonate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent

Procedure

Twenty g. of 6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thiophene was dissolved in 400 ml. of pyridine, together with 23.4 g. of methanesulfonyl chloride and 50 mg. of 4-dimethylaminopyridine. The mixture was stirred under a nitrogen blanket overnight at ambient temperature, and was then poured into 2 liters of water and stirred vigorously. The solids were collected by filtration, and washed successively with water, methanol and diethyl ether. The washed solids were then vacuum dried at 60° to obtain 32.5 g. of the desired intermediate product, m.p. 195°-197°.

Workup

  1. stirringstirred vigorously
  2. filtrationThe solids were collected by filtration
  3. washwashed successively with water, methanol and diethyl ether
  4. customvacuum dried at 60°
  5. customto obtain 32.5 g

Sources & evidence

ORD record
ord-7f97c770bc9c47b581ad727a56256854
Source dataset
uspto-grants-1982_11
Patent number
US04358593

Reaction notes

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