Thiophene → 4-(2-Thienyl)-1-indanyl acetate

HRID 325776Notes

Reaction equation

HRID 325776 reaction equation
[C:1]([O:4][CH:5]1[C:13]2[C:8](=[C:9](N)[CH:10]=[CH:11][CH:12]=2)[CH2:7][CH2:6]1)(=[O:3])[CH3:2].[S:15]1[CH:19]=[CH:18][CH:17]=[CH:16]1.N(OC(C)(C)C)=O>CCCCCCC>[C:1]([O:4][CH:5]1[C:13]2[C:8](=[C:9]([C:16]3[S:15][CH:19]=[CH:18][CH:17]=3)[CH:10]=[CH:11][CH:12]=2)[CH2:7][CH2:6]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 8030ThiopheneHCID 10906Tert-Butyl nitriteHCID 131024584-Amino-1-indanyl acetate

Product 1

HCID 131024594-(2-Thienyl)-1-indanyl acetateYield 17.1%

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 15.0 g (0.079 mole) of 4-amino-1-indanyl acetate in 100 mL (1.25 moles) of thiophene was added dropwise 18.6 mL (0.157 mole) of tert-butyl nitrite. The addition caused an exothermic reaction, raising the temperature of the reaction mixture to 60° C. Upon complete addition, the reaction mixture was stirred for 1.5 hours while cooling to ambient temperature. The reaction mixture was dissolved in 350 mL of n-heptane, and the solution was dried over magnesium sulfate, filtered through a pad of magnesium sulfate, and the filtrate concentrated under reduced pressure to give an oil residue. The oil was purified by column chromatography on silica gel, eluting with hexane, then with 1% ethyl acetatehexane. The appropriate fractions were combined and concentrated under reduced pressure to give 3.5 g of 4-(2-thienyl)-1-indanyl acetate.

Workup

  1. additionThe addition
  2. customan exothermic reaction
  3. additionUpon complete addition
  4. temperaturewhile cooling to ambient temperature
  5. dry with materialthe solution was dried over magnesium sulfate
  6. filtrationfiltered through a pad of magnesium sulfate
  7. concentrationthe filtrate concentrated under reduced pressure
  8. customto give an oil residue
  9. customThe oil was purified by column chromatography on silica gel
  10. washeluting with hexane
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f23f475c3a1d413ca5bc56b512529096
Source dataset
uspto-grants-1984_04
Patent number
US04442296

Reaction notes

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