Methanol → Methyl(7-fluoro-6-hydroxy-4-methyl-1-benzothiophen-3-yl)acetate

HRID 591447Notes

Reaction equation

HRID 591447 reaction equation
[F:1][C:2]1[C:10]2[S:9][CH:8]=[C:7]([CH2:11][C:12]([OH:14])=[O:13])[C:6]=2[C:5]([CH3:15])=[CH:4][C:3]=1[OH:16].OS(O)(=O)=O.[CH3:22]O>>[CH3:22][O:13][C:12](=[O:14])[CH2:11][C:7]1[C:6]2[C:5]([CH3:15])=[CH:4][C:3]([OH:16])=[C:2]([F:1])[C:10]=2[S:9][CH:8]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 89767685(7-Fluoro-6-hydroxy-4-methyl-1-benzothiophen-3-yl)acetic acid

Product 1

HCID 121003808Methyl(7-fluoro-6-hydroxy-4-methyl-1-benzothiophen-3-yl)acetate

Conditions

Temperature
80 °C

Procedure

To a mixture of (7-fluoro-6-hydroxy-4-methyl-1-benzothiophen-3-yl)acetic acid (267 mg) and MeOH (8.0 mL) was added conc. H2SO4 (0.100 mL). The mixture was stirred at 80° C. for 1 h. The mixture was concentrated. The mixture was neutralized with saturated aqueous NaHCO3 and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (255.5 mg).

Workup

  1. concentrationThe mixture was concentrated
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-632ff7f8bc344b4b85b28800990c4b14
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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