Toluene → HCID 86608894, compound

HRID 901068Notes

Reaction equation

HRID 901068 reaction equation
C1([P:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:20]([O:22][C:23](=[O:29])[CH2:24][CH2:25][CH2:26][CH2:27][Br:28])[CH3:21].[C:30]1(C)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>>[Br-:28].[PH4+:7].[C:14]1([C:21]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH2:20][O:22][C:23](=[O:29])[CH2:24][CH2:25][CH2:26][CH3:27])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 3

HCID 1140TolueneHCID 11776TriphenylphosphineHCID 84580Ethyl 5-bromovalerate

Product 1

HCID 86608894HCID 86608894, compoundYield 89.6%

Procedure

In a 100 ml three necked flask equipped with a stir bar, thermocouple and a reflux condenser with a nitrogen inlet was dissolved triphenylphosphine (11.80 g, 45 mmol) in toluene (25 ml), ethyl-5-bromovalerate (12.54 g, 60 mmol) was added to the solution and the reaction mixture was refluxed for 2 hours and then cooled to room temperature. The toluene was decanted away from the oily solid and the residue was slurried in hexane (100 ml). The hexane (3×100 ml) was decanted away three times from the oily residue and oily residue was heated on a Kugelrohr apparatus at 40° C., 0.1 torr for 30 minutes to afford 19.0 g (89.6%) of the title compound.

Workup

  1. additionwas added to the solution
  2. temperaturethe reaction mixture was refluxed for 2 hours
  3. customThe toluene was decanted away from the oily solid
  4. customThe hexane (3×100 ml) was decanted away three times from the oily residue and oily residue
  5. temperaturewas heated on a Kugelrohr apparatus at 40° C.

Sources & evidence

ORD record
ord-783801c9bcfe4e6dae33c55d219a741b
Source dataset
uspto-grants-2008_04
Patent number
US07361686B2

Reaction notes

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