Water → HCID 10107850, compound

HRID 393300Notes

Reaction equation

HRID 393300 reaction equation
[Li][CH2:2]CCC.[Br:6][C:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[C:11](=O)[C:10]2[CH:19]=[CH:20][CH:21]=[CH:22][C:9]=2[CH:8]=1.O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1.CCCCCC>[Br:6][C:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[C:11](=[CH2:2])[C:10]2[CH:19]=[CH:20][CH:21]=[CH:22][C:9]=2[CH:8]=1

Participants

7

Reactant 3

HCID 962WaterHCID 1243721510-Bromo-5H-dibenzo[a,d][7]annulen-5-oneHCID 178418339Butyllithium

Product 1

HCID 10107850HCID 10107850, compound

Reagents, catalysts & solvents 3

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

In a glove box, methyltriphenylphosphonium bromide (8.22 g, 23 mmol, 357.23 g/mol) was dissolved in 150 mL of THF in a flame-dried flask, and n-BuLi (9.21 mL, 23 mmol, 2.5 M in hexane) was added drop wise. The yellow mixture was stirred at ambient temperature for 30 min. and 10-bromo-5H-dibenzo[a,d]cyclohepten-5-one (6.55 g, 23 mmol, 285.14 g/mol) was added as a THF solution. The mixture was stirred and heated at reflux for two days. The cooled solution was taken out of glove box and diluted with 100 mL of hexane. A small amount of water was added to quench the excess reagent, and the mixture was filtered through a plug of silica gel. The silica was rinsed with additional hexane, and the filtrate was concentrated under reduced pressure. The residue was purified by chromatography on silica gel and eluted with ether/hexane (1:1) mixture by volume. Solvent was removed to yield 5.53 g (85 percent, 283.17 g/mol) of the title compound as a pale yellow oil that crystallized upon standing.

Workup

  1. stirringThe mixture was stirred
  2. temperatureheated
  3. temperatureat reflux for two days
  4. customThe cooled solution was taken out of glove box
  5. customto quench the excess reagent
  6. filtrationthe mixture was filtered through a plug of silica gel
  7. washThe silica was rinsed with additional hexane
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe residue was purified by chromatography on silica gel
  10. washeluted with ether/hexane (1:1) mixture by volume
  11. customSolvent was removed

Sources & evidence

ORD record
ord-b5a7269b86a04c8da717e65f0ddd6109
Source dataset
uspto-grants-2004_10
Patent number
US06806327B2

Reaction notes

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