Water → 6-chloro-3-isopropyl-1H-indene

HRID 979170Notes

Reaction equation

HRID 979170 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=O)[CH2:6][CH2:5]2.[CH:12]([Mg]Cl)([CH3:14])[CH3:13].O>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8]([C:7]([CH:12]([CH3:14])[CH3:13])=[CH:6][CH2:5]2)=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 1425995-Chloro-1-indanoneHCID 178418918HCID 178418918, compound

Product 1

HCID 138536776-chloro-3-isopropyl-1H-indene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-chloro-1-indanone (3.59 g) in anhydrous tetrahydrofuran (40 ml) was added to a solution of isopropyl magnesium chloride (103 ml, 2M ethereal solution) under nitrogen at a rate to produce gentle refluxing. After the addition, the reaction solution was further stirred at room temperature for 11/4 hr, then poured into water (200 ml) and extracted with diethyl ether (3×150 ml). The combined ether solutions was washed with water, and condensed to an oil. This oil dissolved in benzene (250 ml) with a catalytic amount of p-toluenesulfonic acid was refluxed for 1.5 hr and then poured into water (200 ml). A few drops of diethylamine were added. The aqueous solution was separated and extracted with diethyl ether (3×100 ml). The combined organic phases were washed sequentially with dilute hydrochloric acid, saturated sodium bicarbonate solution and water, then dried (MgSO4) and condensed under reduced pressure. The residue was purified on a flash column (eluted with 5% ether in hexane) to give 6-chloro-3-isopropyl-1H-indene (2.94 g).

Workup

  1. customto produce gentle refluxing
  2. additionAfter the addition
  3. extractionextracted with diethyl ether (3×150 ml)
  4. washThe combined ether solutions was washed with water, and condensed to an oil
  5. dissolutionThis oil dissolved in benzene (250 ml) with a catalytic amount of p-toluenesulfonic acid
  6. temperaturewas refluxed for 1.5 hr
  7. additionpoured into water (200 ml)
  8. additionA few drops of diethylamine were added
  9. customThe aqueous solution was separated
  10. extractionextracted with diethyl ether (3×100 ml)
  11. washThe combined organic phases were washed sequentially with dilute hydrochloric acid, saturated sodium bicarbonate solution and water
  12. customdried
  13. custom(MgSO4) and condensed under reduced pressure
  14. customThe residue was purified on a flash column (eluted with 5% ether in hexane)

Sources & evidence

ORD record
ord-23f654a32bc741dea24fe9d70aeebcab
Source dataset
uspto-grants-1987_05
Patent number
US04666925

Reaction notes

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