Water → 1-Ethyl-1H-indene

HRID 1955287Notes

Reaction equation

HRID 1955287 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[Li][CH2:11][CH2:12]CC.C(Br)C.O>C1COCC1.CCCCCC>[CH2:11]([CH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1)[CH3:12]

Participants

7

Reactant 4

HCID 962WaterHCID 6332Ethyl BromideHCID 7219IndeneHCID 178418339Butyllithium

Product 1

HCID 2364041-Ethyl-1H-indeneYield 78%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-70 °C

Procedure

To a solution of 30 ml (0.26 moles) of indene in 250 ml of THF, 105 ml is added (0.26 moles) of 2.5 M BuLi in hexane, with temperature being kept comprised within the range of from 30° C. to 40° C. The reaction mixture is then cooled down to -70° C. and 19 ml (0.25 moles) of ethyl bromide is added dropwise during approximately 3 hours. The temperature is allowed to rise up to approximately 20-25° C. and then the mixture is hydrolysed with water and extracted with petroleum ether. After washing until neutral, drying and evaporation of the organic phase, the obtained residue is distilled. The fraction boiling at 92-95° C./30 mm Hg is collected, and 28 g of 1-ethylindene is obtained (yield 78%)

Workup

  1. custombeing kept comprised within the range of from 30° C. to 40° C
  2. customto rise up to approximately 20-25° C.
  3. extractionextracted with petroleum ether
  4. washAfter washing until neutral,
  5. customdrying
  6. customevaporation of the organic phase
  7. distillationthe obtained residue is distilled
  8. customThe fraction boiling at 92-95° C./30 mm Hg is collected

Sources & evidence

ORD record
ord-006277b950c24fd69412a0e91f8b62c7
Source dataset
uspto-grants-2000_09
Patent number
US06124413

Reaction notes

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