Pyridine → HCID 18387761, compound

HRID 2271015Notes

Reaction equation

HRID 2271015 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.[C:13](OC(=O)C)(=[O:15])[CH3:14].N1C=CC=CC=1>O1CCCC1>[C:13]([O:12][C:9]1[CH:10]=[CH:11][C:6]([C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)=[CH:7][CH:8]=1)(=[O:15])[CH3:14]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 35641974-Thiophen-2-ylphenol

Product 1

HCID 18387761HCID 18387761, compoundYield 79.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 4-(2-thienyl)phenol (1.00 g) and acetic anhydride (869 mg) in tetrahydrofuran (10 ml) was added pyridine (494 mg) with ice-cooling. The mixture was stirred for 1 hour at said temperature and 1 hour at ambient temperature. After concentration, the mixture was partitioned between AcOEt and H2O. The separated organic layer was washed with 1% aqueous citric acid, 3% aqueous NaHCO3 solution and brine, dried over sodium sulfate and concentrated. The residue was triturated with hexane to give 985 mg of 2-(4-acetoxyphenyl)thiophene as a powder.

Workup

  1. temperaturecooling
  2. customtemperature and 1 hour
  3. customat ambient temperature
  4. concentrationAfter concentration
  5. customthe mixture was partitioned between AcOEt and H2O
  6. washThe separated organic layer was washed with 1% aqueous citric acid, 3% aqueous NaHCO3 solution and brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. customThe residue was triturated with hexane

Sources & evidence

ORD record
ord-bd1ad6567ac44e729bc3b7b0944527a2
Source dataset
uspto-grants-2001_12
Patent number
US06333324B1

Reaction notes

Loading…