Hexane → HCID 21973146, compound

HRID 11261Notes

Reaction equation

HRID 11261 reaction equation
[Cl-:1].[NH4+:2].C[Al](C)C.CCCCCC.[CH2:13]([O:20][C:21]1[CH:22]=[CH:23][C:24]([O:29][CH2:30][CH3:31])=[C:25]([CH:28]=1)[C:26]#[N:27])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1(C)C=CC=CC=1.ClCCl>[ClH:1].[CH2:13]([O:20][C:21]1[CH:28]=[C:25]([C:24]([O:29][CH2:30][CH3:31])=[CH:23][CH:22]=1)[C:26]([NH2:2])=[NH:27])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

7

Reactant 4

HCID 8058HexaneHCID 25517Ammonium ChlorideHCID 16682925TrimethylaluminumHCID 219731695-Benzyloxy-2-ethoxybenzonitrile

Product 1

HCID 21973146HCID 21973146, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

46.46 g of ammonium chloride (868.5 mol) are suspended in 650 ml of toluene, and the mixture is cooled to 0–5° C. Trimethylaluminum is added dropwise as a 2M solution in hexane (445 ml, 888.3 mmol), and the mixture is then stirred at room temperature until the evolution of gas has ceased. 5-Benzyloxy-2-ethoxybenzonitrile (100 g, 394.8 mmol) (example 32A) is added, and the mixture is stirred at 80° C. overnight. The cooled reaction mixture is with ice-cooling, added to a suspension of 200 g of silica gel and 2 l of dichloromethane, and the mixture is stirred for 30 min. The mixture is filtered off with suction and the filter cake is washed with methanol. The organic phases are combined and concentrated. The resulting residue is triturated using a mixture of dicloromethane/methanol 9:1, filtered and concentrated using a rotary evaporator. The residue is then triturated with ether, and the colorless solid is filtered off with suction.

Workup

  1. temperaturethe mixture is cooled to 0–5° C
  2. stirringthe mixture is stirred at 80° C. overnight
  3. customThe cooled reaction mixture
  4. temperaturecooling
  5. stirringthe mixture is stirred for 30 min
  6. filtrationThe mixture is filtered off with suction
  7. washthe filter cake is washed with methanol
  8. concentrationconcentrated
  9. customThe resulting residue is triturated
  10. additiona mixture of dicloromethane/methanol 9:1
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customa rotary evaporator
  14. customThe residue is then triturated with ether
  15. filtrationthe colorless solid is filtered off with suction

Sources & evidence

ORD record
ord-b97f90e65b064970a2b84bf42bde3570
Source dataset
uspto-grants-2006_08
Patent number
US07098207B2

Reaction notes

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