Isoprene → 11,11-Diphenylundec-1-ene

HRID 273823Notes

Reaction equation

HRID 273823 reaction equation
[Li].[C:2]1([C:8]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)(OC)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH:17]=[CH2:18])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C=CC(=C)C.[Cl-].[NH4+]>N.C1COCC1.CO>[C:2]1([CH:8]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH:17]=[CH2:18])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 6557IsopreneHCID 25517Ammonium ChlorideHCID 3028194Lithium2×HCID 2008832511,11-Diphenyl-11-methoxyundec-1-ene

Product 1

HCID 2008832411,11-Diphenylundec-1-eneYield 105.4%

Reagents, catalysts & solvents 3

HCID 222AmmoniaSolvent2×HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium wire, 0.75 g, was dissolved in 300 mL of ammonia at -78° C. A solution of 10.1 g of 11,11-diphenyl-11-methoxyundec-1-ene in 20 mL of THF was added to the lithium solution and the mixture was stirred at reflux for 30 min. To a reaction vessel were added sequentially 5 mL isoprene, 5 mL of methanol, and 10 g of ammonium chloride and the ammonia allowed to evaporate at room temperature. Diethyl ether was added to the mixture and the solution was washed with water and brine (saturated aqueous sodium chloride). The organic layer was dried and concentrated in vacuo to give 9.7 g of 11,11-diphenylundec-1-ene which is characterized by:

Workup

  1. temperatureat reflux for 30 min
  2. customto evaporate at room temperature
  3. additionDiethyl ether was added to the mixture
  4. washthe solution was washed with water and brine (saturated aqueous sodium chloride)
  5. customThe organic layer was dried
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d7ceb933c0c24dbebec2cb94b509ff9e
Source dataset
uspto-grants-1995_02
Patent number
US05387617

Reaction notes

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