3-Pyridinemethanol → HCID 53682346, compound

HRID 1200056Notes

Reaction equation

HRID 1200056 reaction equation
[S:1]1[CH:5]=[C:4]([CH:6]=[CH:7][C:8]2[S:12][C:11]([C:13](Cl)=[O:14])=[CH:10][CH:9]=2)[C:3]2[CH:16]=[CH:17][CH:18]=[CH:19][C:2]1=2.N1C=CC=C(C[OH:27])C=1>N1C=CC=CC=1>[S:1]1[CH:5]=[C:4]([CH:6]=[CH:7][C:8]2[S:12][C:11]([C:13]([OH:27])=[O:14])=[CH:10][CH:9]=2)[C:3]2[CH:16]=[CH:17][CH:18]=[CH:19][C:2]1=2

Participants

4

Reactant 2

HCID 75103-PyridinemethanolHCID 539913705-[2-(Benzo[b]thiophen-3-yl)ethenyl]thiophene-2-carboxylic acid chloride

Product 1

HCID 53682346HCID 53682346, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The acid chloride of 5-[2-(benzo[b]thiophen-3-yl)ethenyl]thiophene-2-carboxylic acid was prepared as described in Example 9. To a suspension of 5-[2-(benzo[b]thiophen-3-yl)ethenyl]thiophene2-carboxylic acid chloride (5.00 g) and pyridine (50 ml) was added 3-pyridylcarbinol (1.79 g). After refluxing overnight, the mixture was evaporated, and the residue was dissolved in ether, filtered, and concentrated. The residue was purified by high performance liquid chromatography (silica gel, eluted with 2:1 ethyl acetate:hexane). The appropriate fractions were combined and evaporated. The residue was recrystallized from toluene/hexane to afford 1.4 g (23%) of the product, mp 97°-98° C.

Workup

  1. temperatureAfter refluxing overnight
  2. customthe mixture was evaporated
  3. dissolutionthe residue was dissolved in ether
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by high performance liquid chromatography (silica gel, eluted with 2:1 ethyl acetate:hexane)
  7. customevaporated
  8. customThe residue was recrystallized from toluene/hexane

Sources & evidence

ORD record
ord-1592a9c9c70a4632af2721e3e6f41298
Source dataset
uspto-grants-1990_02
Patent number
US04904674

Reaction notes

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