Pyridine → Indan-5-yl acetate

HRID 228707Notes

Reaction equation

HRID 228707 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([OH:10])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.N1C=CC=CC=1.[C:17](Cl)(=[O:19])[CH3:18]>ClCCl>[C:17]([O:10][C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[CH2:1][CH2:2][CH2:3]2)(=[O:19])[CH3:18]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 151185-Indanol

Product 1

HCID 79504Indan-5-yl acetateYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Indanol (500 mg) was dissolved in dichloromethane (5 ml) to prepare a solution. Pyridine (439 mg) and acetyl chloride (349 mg) were added to the solution, and the mixture was stirred at room temperature for 6 hr. The solvent was removed by distillation under the reduced pressure, water was then added to the residue, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with water and was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography using chloroform to give indan-5-yl acetate (599 mg, yield 92%).

Workup

  1. customto prepare a solution
  2. customThe solvent was removed by distillation under the reduced pressure, water
  3. additionwas then added to the residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe ethyl acetate layer was then washed with water
  6. dry with materialwas dried over anhydrous magnesium sulfate
  7. customThe solvent was removed by distillation under the reduced pressure
  8. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-60557b6763b54c61ba28d710d22fd49d
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

Loading…