Indene → 2-[2-(1H-inden-3-yl)ethyl]pyridine

HRID 1704652Notes

Reaction equation

HRID 1704652 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.CC(C)([O-])C.[K+].[CH:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)=[CH2:17]>C(O)(=O)C>[N:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[CH2:16][CH2:17][C:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]=1

Participants

5

Reactant 3

HCID 7219IndeneHCID 75212-VinylpyridineHCID 23665647Potassium tert-butoxide

Product 1

HCID 121355622-[2-(1H-inden-3-yl)ethyl]pyridine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

This compound is prepared as described by Dressler and Kurland J.O.C. 29, 175 (1964). Under nitrogen gas, 500 g. indene plus 5 g. potassium t-butoxide are stirred and heated to 130°. 2-Vinyl pyridine (220 g., 2.0 M) is added dropwise over a period of 1 hour keeping the temperature at 135°-145° C. during addition and for 2 hours after addition is completed. The reaction mixture is cooled and 25 ml. acetic acid is added, followed by filtration. A flash distillation yields 395 g. (84%) crude product boiling 160°-175°/0.3 mm. This is redistilled to give 353 g. (75%) of oil (3-[2[(pyridyl)ethyl]indene) boiling point 135°-140°/0.1 mm.

Workup

  1. customThis compound is prepared
  2. temperatureheated to 130°
  3. customat 135°-145° C.
  4. additionduring addition
  5. additionfor 2 hours after addition
  6. temperatureThe reaction mixture is cooled
  7. filtrationfollowed by filtration
  8. distillationA flash distillation
  9. customyields 395 g
  10. customboiling 160°-175°
  11. distillationThis is redistilled
  12. customto give 353 g

Sources & evidence

ORD record
ord-be8c321db5d349beba33abd044d00579
Source dataset
uspto-grants-1978_11
Patent number
US04127578

Reaction notes

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