Indene → HCID 21834944, compound

HRID 1829590Notes

Reaction equation

HRID 1829590 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[CH2:10](Br)[CH2:11][CH2:12][CH3:13]>C1COCC1>[CH2:10]([CH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1)[CH2:11][CH2:12][CH3:13]

Participants

4

Reactant 2

HCID 7219IndeneHCID 8002Butyl bromide

Product 1

HCID 21834944HCID 21834944, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

N-BuLi (173 mmol) was added to indene (173 mmol) in THF (70 mL) at ambient temperature using an oil bath as a heat sink. The reaction was stirred for 40 minutes, then added to n-butyl bromide (223 mmol) in THF (70 mL) at 0° C. The reaction was stirred overnight at ambient temperature, followed by standard aqueous workup. Evaporation of solvent followed by distillation under reduced pressure gave pure n-butylindene. n-BuLi (13.5 mmol) was added to n-butylindene (13.5 mmol) in THF (50 mL) and stirred for 1 hour. The solution was then added to ((tBu)3PN)TiCl3 (which was prepared by the reaction of TiCl4 with (tBu)3PN-TMS) slurried in toluene at −78° C. After stirring overnight at ambient temperature and the solvent was removed under vacuum. The residue was extracted into toluene, filtered and the filtrate concentrated. Addition of heptane precipitated the product that was isolated by filtration.

Workup

  1. stirringThe reaction was stirred overnight at ambient temperature
  2. customEvaporation of solvent
  3. distillationfollowed by distillation under reduced pressure

Sources & evidence

ORD record
ord-052114e69f19405db6bce21309cf4d5b
Source dataset
uspto-grants-2006_06
Patent number
US07064096B1

Reaction notes

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