HCID 18544227, compound → HCID 178506816, compound

HRID 1268146Notes

Reaction equation

HRID 1268146 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[CH2:8][CH:7]=[C:6]2[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[Li:20]CCCC>C1(C)C=CC=CC=1.CCCCCC>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[CH:8]([Li:20])[CH:7]=[C:6]2[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 18544227HCID 18544227, compoundHCID 178418339Butyllithium2×

Product 1

HCID 178506816HCID 178506816, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Procedure

5,6-dimethoxy-3-phenyl-1H-indene (1.26 g, 4.99 mmol) was dissolved in a mixture of 15 mL of toluene and 25 mL of hexane and 3.06 mL of 1.6 M n-BuLi were added dropwise via syringe over a 3 min period. The solution developed a yellow-light green precipitate during addition of n-BuLi. The reaction mixture was stirred for 3 h and then filtered, washed with 60 mL of hexane and dried in vacuum to afford the desired product as a yellow solid (1.24 g) in 98 percent yield.

Workup

  1. additionwere added dropwise via syringe over a 3 min period
  2. filtrationfiltered
  3. washwashed with 60 mL of hexane
  4. customdried in vacuum

Sources & evidence

ORD record
ord-6ede418f87e54cdc900fd9c687b8e0f0
Source dataset
uspto-grants-2003_04
Patent number
US06555634B1

Reaction notes

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