6-Methoxy-1-benzothiophene → Benzo(b)thiophene-6-ol

HRID 732815

Reaction equation

HRID 732815 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.[Na].C(S)C>CN(C=O)C>[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 136342376-Methoxy-1-benzothiopheneHCID 45051917HCID 45051917, compound2×

Product 1

HCID 88004Benzo(b)thiophene-6-olYield 36.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

Dissolve 6-methoxy-benzo[b]thiophene (J. Med. Chem. 32:2548, 1989; 26.1 g, 146 mmol) in DMF (500 mL). Add ethanethiol sodium salt (37 g, 440 mmol) and heat to 150° C. with stirring overnight. Add additional ethanethiol sodium salt (12.8 g, 152 mmol) and continue to heat at 150° C. overnight. Concentrate in vacuo to ¼ volume. Partition reaction mixture between ethyl acetate (500 mL) and water (500 mL), separate layers, wash organic layer with water (2×500 mL), brine (500 mL), and dry with magnesium sulfate. Filter and concentrate in vacuo to give 8 g of benzo[b]thiophen-6-ol. Back extract aqueous layers with ethyl acetate (3×1000 mL) wash organics with brine, and dry with magnesium sulfate. Concentrate in vacuo to obtain an additional 15 grams of benzo[b]thiophen-6-ol. Distill off remaining DMF to yield 22.7 g (100%) of benzo[b]thiophen-6-ol.

Workup

  1. concentrationConcentrate in vacuo
  2. customPartition
  3. customreaction mixture between ethyl acetate (500 mL) and water (500 mL)
  4. customseparate layers
  5. washwash organic layer with water (2×500 mL), brine (500 mL)
  6. dry with materialdry with magnesium sulfate
  7. filtrationFilter
  8. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-6527434e7a064093bc3627e0d06acd05
Source dataset
uspto-grants-2009_09
Patent number
US07585977B2

Linked notes

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