Indene → Cinnamyl indene

HRID 361290Notes

Reaction equation

HRID 361290 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C([Li])CCC.[CH2:15](Cl)[CH:16]=[CH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1COCC1>[CH2:15]([CH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1)[CH:16]=[CH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 7219IndeneHCID 94242Benzene, (3-chloro-1-propenyl)-HCID 178418339Butyllithium

Product 1

HCID 54368125Cinnamyl indeneYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 98% indene (364 mmoles) in 300 ml of THF was cooled to -78° C. under argon. An equimolar amount of n-butyllithium was added to the solution. The resulting mixture was allowed to warm to room temperature. It was then charged to an equimolar amount of 95% cinnamyl chloride (58.45 g) in 100 ml of THF at -30° C. The mixture was then allowed to warm to room temperature and react for one hour to form cinnamyl indene. The cinnamyl indene was concentrated down to a residue under strong vacuum, and then washed and concentrated twice with 100 ml of hexane. The residue was washed a third time with 100 ml of warm hexane and filtered while hot. The filtrate was again concentrated down to a residue under vacuum. The cinnamyl indene filtrate melted at 55°-69° C. Recovery yield was 62%.

Workup

  1. temperatureto warm to room temperature
  2. customreact for one hour

Sources & evidence

ORD record
ord-3f2e85dcf5044339860a0b3a9bec2950
Source dataset
uspto-grants-1999_02
Patent number
US05866497

Reaction notes

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