Diethyl Ether → 2-ethyl-1h-indene

HRID 850125Notes

Reaction equation

HRID 850125 reaction equation
Br[C:2]1[CH2:3][C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.[CH2:11](OCC)[CH3:12]>Cl[Ni]1(Cl)[P](C2C=CC=CC=2)(C2C=CC=CC=2)CCC[P]1(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:11]([C:2]1[CH2:3][C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH3:12]

Participants

4

Reactant 2

HCID 3283Diethyl Ether2×HCID 5755861H-Indene, 2-bromo-

Product 1

HCID 5823282-ethyl-1h-indene

Reagents, catalysts & solvents 1

HCID 178418745HCID 178418745, compoundCatalyst

Procedure

2-Bromoindene (8.1235 g, 0.04211 moles) and Ni(dppp)Cl2 (0.1536 g, 2.83×10-4 moles) were stirred in diethylether (100 mL) at -78° C. under a nitrogen atmosphere as ethylMgBr (0.045 moles, 15.00 mL of 3.0 M solution in diethylether) was added. The dry-ice bath was then removed and the reaction mixture allowed to warm to room temperature. The reaction mixture started off as a heterogeneous brick-red color and then turned to a homogeneous yellow/gold solution and then back to the heterogeneous brick-red mixture during the course of the warm-up. Gas chromatographic analysis after 2 hours of stirring at room temperature showed that the reaction was substantially quantitative. After the reaction period the mixture was poured onto ice and then extracted with 1 M HCL (1×100 mL) and 1 M NaHCO3 (1×100 mL) and then dried with MgSO4 and filtered. The desired product was isolated as a light yellow oil (5.65 g, 93.1 percent).

Workup

  1. additionwas added
  2. customThe dry-ice bath was then removed
  3. customAfter the reaction period the mixture
  4. additionwas poured onto ice
  5. extractionextracted with 1 M HCL (1×100 mL) and 1 M NaHCO3 (1×100 mL)
  6. dry with materialdried with MgSO4
  7. filtrationfiltered

Sources & evidence

ORD record
ord-f11a9e46bc854cc28df92cfe10e29897
Source dataset
uspto-grants-2000_01
Patent number
US06015868

Reaction notes

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