Indene → HCID 21930637, compound

HRID 2304031Notes

Reaction equation

HRID 2304031 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][CH2:13][CH3:14].Br[CH2:16][CH2:17][CH2:18]Br>CCCCCC.C1COCC1>[CH:1]1([CH2:14][CH2:13][CH2:12][CH:11]2[C:8]3[C:18](=[CH:3][CH:2]=[CH:1][CH:9]=3)[CH:17]=[CH:16]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

6

Reactant 3

HCID 7219IndeneHCID 80011,3-DibromopropaneHCID 178418339Butyllithium

Product 1

HCID 21930637HCID 21930637, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

12.8 mL of indene (91% by GC, 0.1 mol) and 130 mL of THF were placed in a 250 mL flask equipped with stirring bar and dropping funnel. After cooling to −78° C., 62.6 mL of 1.6 M BuLi solution in hexane were added dropwise. At the end of the addition the reaction mixture was allowed to warm to room temperature. The so obtained dark solution was transferred into a 250 mL dropping funnel connected to a 0.5 L flask, and then added dropwise over 1 h to a solution of 10.1 g (5 mL, 0.05 mol) of 1,3-dibromopropane in 100 mL THF under vigorous stirring, while keeping the temperature of the reaction mixture in the range −70 to −75° C. throughout the addition. The cooling bath was removed and the mixture stirred overnight. 10 mL MeOH were then added and the solvents removed under reduced pressure. The obtained solid was suspended in 100 mL of a 4:1 hexane-CH2Cl2 mixture and passed through silica gel using the same mixture as eluent. The solvents were removed under reduced pressure and the resulting slightly yellow crystalline product was washed twice with small portions of cold ethanol and dried in vacuum. Yield 72%, purity 95.2% (G.C.).

Workup

  1. customequipped
  2. additionAt the end of the addition the reaction mixture
  3. temperatureto warm to room temperature
  4. customThe so obtained dark solution
  5. customconnected to a 0.5 L flask
  6. customin the range −70 to −75° C.
  7. additionthroughout the addition
  8. customThe cooling bath was removed
  9. stirringthe mixture stirred overnight
  10. addition10 mL MeOH were then added
  11. customthe solvents removed under reduced pressure
  12. customThe solvents were removed under reduced pressure
  13. washthe resulting slightly yellow crystalline product was washed twice with small portions of cold ethanol
  14. customdried in vacuum

Sources & evidence

ORD record
ord-2d043f7d222f43ecb1281787e352776a
Source dataset
uspto-grants-2002_08
Patent number
US06433203B1

Reaction notes

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