5-Indanecarboxaldehyde → 2,3-Dihydro-5-(2-methyl-1-propen-1-yl)-1H-indene

HRID 2215283Notes

Reaction equation

HRID 2215283 reaction equation
[Li][CH2:2][CH2:3][CH2:4]C.[CH2:6]1[C:14]2[C:9](=[CH:10][C:11]([CH:15]=O)=[CH:12][CH:13]=2)[CH2:8][CH2:7]1>C1COCC1>[CH3:2][C:3]([CH3:4])=[CH:15][C:11]1[CH:10]=[C:9]2[C:14](=[CH:13][CH:12]=1)[CH2:6][CH2:7][CH2:8]2

Participants

4

Reactant 2

HCID 1216245-IndanecarboxaldehydeHCID 178418339Butyllithium

Product 1

HCID 219502342,3-Dihydro-5-(2-methyl-1-propen-1-yl)-1H-indeneYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

In a flamed dried flask under argon isopropyltriphenylphosphonium iodide (6.48 g, 15 mmol) in 30 mL of dry THF was cooled to 0° C. Then n-BuLi (2.5 M) in hexanes (6.0 mL) was added via syringe. The reaction mixture was stirred 0° C. for 45 min. Then a solution of the 2,3-dihydro-1H-indene-5-carboxaldehyde (J. Med. Chem. 1993, 36, 3700–3706) was added (1.7, 12.0 mmol) in THF (20 mL) was added drop-wise and the reaction was stirred under Argon at RT overnight. The reaction was filtered, the filtrate was concentrated in vacuo and the residue purified by flash colum chromatography (ethyl acetate/hexane, 1:99) to yield the above titled compound as a pale yellow oil (1.7 g, 67%).

Workup

  1. additionwas added drop-wise
  2. stirringthe reaction was stirred under Argon at RT overnight
  3. filtrationThe reaction was filtered
  4. concentrationthe filtrate was concentrated in vacuo
  5. customthe residue purified by flash colum chromatography (ethyl acetate/hexane, 1:99)

Sources & evidence

ORD record
ord-5c5489d166824247b046f7021b3fac9a
Source dataset
uspto-grants-2006_09
Patent number
US07109238B2

Reaction notes

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