Pyridinium chloride → Benzo(b)thiophene-6-ol

HRID 252159

Reaction equation

HRID 252159 reaction equation
C[O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH:10]=[CH:9][S:8][C:7]=2[CH:11]=1.Cl.N1C=CC=CC=1>O>[S:8]1[CH:9]=[CH:10][C:6]2[CH:5]=[CH:4][C:3]([OH:2])=[CH:11][C:7]1=2

Participants

4

Reactant 2

HCID 10176127Pyridinium chlorideHCID 136342376-Methoxy-1-benzothiophene

Product 1

HCID 88004Benzo(b)thiophene-6-olYield 98.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

6-Methoxybenzo[b]thiophene (6.15 g, 37.45 mmol) and pyridine hydrochloride (18.5 g) were heated together at 210° C. for 1 h. The mixture was cooled to 100° C., diluted with water (125 mL) and extracted with dichloromethane (3×70 mL). The combined extracts were washed with water (125 mL), dried (MgSO4) and evaporated in vacuo to give the title compound (5.54 g, 98%)

Workup

  1. extractionextracted with dichloromethane (3×70 mL)
  2. washThe combined extracts were washed with water (125 mL)
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-5e1e09f2b3994491a6902c43b3fe3a66
Source dataset
uspto-grants-2011_01
Patent number
US07868017B2

Linked notes

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