Isobutanol → HCID 178435413, compound

HRID 1974810Notes

Reaction equation

HRID 1974810 reaction equation
[CH2:1]([C:3]1[S:15][C:6]2=[N:7][CH:8]=[C:9]([C:12]([OH:14])=[O:13])[C:10]([OH:11])=[C:5]2[CH:4]=1)[CH3:2].B(F)(F)F.CCOCC.[CH2:25](O)[CH:26]([CH3:28])[CH3:27]>>[CH2:1]([C:3]1[S:15][C:6]2=[N:7][CH:8]=[C:9]([C:12]([O:14][CH2:25][CH:26]([CH3:28])[CH3:27])=[O:13])[C:10]([OH:11])=[C:5]2[CH:4]=1)[CH3:2]

Participants

4

Reactant 3

HCID 6560IsobutanolHCID 8000Boron trifluoride etherateHCID 178435415HCID 178435415, compound

Product 1

HCID 178435413HCID 178435413, compoundYield 31%

Procedure

A mixture of 2-ethyl-4-hydroxythieno[2,3-b]pyridine-5-carboxylic acid (200 mg, 0.9 mmol) and boron trifluoride-ethyl ether (47%, 0.5 ml) in isobutyl alcohol (10 ml) was heated under reflux for 5 hours. The reaction mixture was allowed to cool and concentrated to dryness. The resulting residue was purified by flash column chromatography on silica gel. The column was eluted with chloroform/ethyl acetate (3:1) to give 80 mg (31%) of the title compound as colorless crystals.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hours
  3. temperatureto cool
  4. concentrationconcentrated to dryness
  5. customThe resulting residue was purified by flash column chromatography on silica gel
  6. washThe column was eluted with chloroform/ethyl acetate (3:1)

Sources & evidence

ORD record
ord-ebf1f3196b4c4e30a44fa1c7e024e184
Source dataset
uspto-grants-1994_02
Patent number
US05284661

Reaction notes

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