HCID 11436030, compound → HCID 59300343, compound

HRID 2236503Notes

Reaction equation

HRID 2236503 reaction equation
[CH2:1]([N:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][CH:7]=1)[CH:2]=[CH2:3].[CH2:13]([Mg]Br)[CH:14]=[CH2:15]>C1COCC1>[CH2:1]([NH:4][CH:5]([C:6]1[CH:7]=[CH:8][C:9]([Br:12])=[CH:10][CH:11]=1)[CH2:15][CH:14]=[CH2:13])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 11436030HCID 11436030, compoundHCID 178455850HCID 178455850, compound

Product 1

HCID 59300343HCID 59300343, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Allyl-(4-bromo-benzylidene)-amine (1.13 g, 5.0 mmol) is dissolved in THF (15 mL) and the mixture is cooled to 0° C. with an ice bath. Allyl magnesium bromide (6.0 mL, 1.0 M in ethyl ether, 6.0 mmol) is added. The resulting mixture is stirred at 0° C. for 1 hour and warmed to room temperature followed by reaction quenching. EtOAc and water were added and the EtOAc layer is washed with brine and dried. After removal of EtOAc, the product (1.0 g, 75%) is obtained. MS (ESI): 266, 268 (M+1)+1.

Workup

  1. temperaturewarmed to room temperature
  2. customfollowed by reaction
  3. customquenching
  4. additionEtOAc and water were added
  5. washthe EtOAc layer is washed with brine
  6. customdried
  7. customAfter removal of EtOAc

Sources & evidence

ORD record
ord-e9eae0d6a9f74e6586d2c6807db236c6
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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