Alpha-Methylstyrene → HCID 12551067, compound

HRID 898841Notes

Reaction equation

HRID 898841 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[CH2:3].N12CCCN=C1CCCCC2.Br[CH:22]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[C:23]([O:25][CH2:26][CH3:27])=[O:24]>C1(C)C=CC=CC=1.[Cu](Br)Br>[CH2:26]([O:25][C:23]([C:22]1([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:1][C:2]1([CH3:3])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:24])[CH3:27]

Participants

6

Reactant 3

HCID 7407Alpha-MethylstyreneHCID 69637Diethyl bromomalonateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 12551067HCID 12551067, compoundYield 45.2%

Reagents, catalysts & solvents 2

HCID 24611Copper bromide (CuBr2)CatalystHCID 1140TolueneSolvent

Procedure

To a solution of α-methylstyrene (570 mL, 4.4 mol), 1,8-diazabicyclo[5.4.0]undec-7-ene (240 mL, 1.6 mol) and copper (II) bromide (9.8 g, 44 mmol) in toluene (700 mL) was added diethyl bromomalonate (210 g, 0.88 mol) at 0° C., and the mixture was stirred for 22 hours at room temperature. The obtained solution was washed with saturated aqueous ammonium chloride solution and saturated aqueous sodium chloride solution, and dried over sodium sulfate. Then, the solution was filtrated and the solvent was evaporated. The obtained residue was separated and purified by silica gel chromatography (hexane:ethyl acetate=20:1) to give the title compound (110 g, yield 45%) as a colorless oil.

Workup

  1. washThe obtained solution was washed with saturated aqueous ammonium chloride solution and saturated aqueous sodium chloride solution
  2. dry with materialdried over sodium sulfate
  3. filtrationThen, the solution was filtrated
  4. customthe solvent was evaporated
  5. customThe obtained residue was separated
  6. custompurified by silica gel chromatography (hexane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-77f4c79456294192adc2389d3f0d1b02
Source dataset
uspto-grants-2008_04
Patent number
US07351825B2

Reaction notes

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