Hydrogen Peroxide → HCID 11533228, compound

HRID 1516653Notes

Reaction equation

HRID 1516653 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:16]2[CH:17]=[C:18]([C:24]3[CH:29]=[CH:28][C:27]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:26][CH:25]=3)[CH:19]=[CH:20][C:21]=2[CH:22]=[CH2:23])[CH:8]=[CH:9][C:10]=1[N:11]([CH2:14][CH3:15])[CH2:12][CH3:13])([CH3:4])([CH3:3])[CH3:2].B12CC(CCC1)CC[CH2:36]2.[OH-:44].[Na+].OO>C1COCC1>[C:1]([C:5]1[CH:6]=[C:7]([C:16]2[CH:17]=[C:18]([C:24]3[CH:29]=[CH:28][C:27]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:26][CH:25]=3)[CH:19]=[CH:20][C:21]=2[CH2:22][CH2:23][CH2:36][OH:44])[CH:8]=[CH:9][C:10]=1[N:11]([CH2:14][CH3:15])[CH2:12][CH3:13])([CH3:3])([CH3:4])[CH3:2]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 22391873HCID 22391873, compoundHCID 66671882HCID 66671882, compound

Product 1

HCID 11533228HCID 11533228, compoundYield 77.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

8 g of ethyl 3″-tert-butyl-4″-diethylamino-4′-vinyl[1,1′;3′,1″]terphenyl-4-carboxylate (17 mmol) are dissolved in 400 mL of THF with stirring and, under cold conditions (ice bath), 6.2 g of 9 borabicyclo[3.3.1]nonane (51 mmol) are added and the ice bath is removed to raise the temperature of the reaction medium to room temperature, at which point the reaction medium is stirred for 1 hour 30 minutes. The temperature of the reaction medium is again reduced to 0° C., 52.8 mL of NaOH (53 mmol) are added portionwise, and the medium is stirred for 10 minutes at 0° C.; 37.3 mL of H2O2 (426 mmol) are then added dropwise and the reaction medium is warmed to room temperature and then stirred for 2 hours 30 minutes. The reaction is stopped by adding 500 mL of ice-water and then extracted with 500 mL of ethyl acetate. The organic phases are washed with 1 L of water and then dried over magnesium sulfate. The solvents are evaporated off and the residue is then purified by chromatography on silica gel (eluent: 7/3 heptane/ethyl acetate). 6.4 g of ethyl 3″-tert-butyl-4″-diethylamino-4′-(3-hydroxypropyl)-[1,1′;3′,1″]terphenyl-4-carboxylate are obtained (yield=75%).

Workup

  1. additionare added
  2. customthe ice bath is removed
  3. customis again reduced to 0° C.
  4. stirringthe medium is stirred for 10 minutes at 0° C.
  5. customthe reaction
  6. temperaturemedium is warmed to room temperature
  7. stirringstirred for 2 hours 30 minutes
  8. extractionextracted with 500 mL of ethyl acetate
  9. washThe organic phases are washed with 1 L of water
  10. dry with materialdried over magnesium sulfate
  11. customThe solvents are evaporated off
  12. customthe residue is then purified by chromatography on silica gel (eluent: 7/3 heptane/ethyl acetate)

Sources & evidence

ORD record
ord-5ec1baa72b6f471cb26eac38b894f07e
Source dataset
uspto-grants-2012_07
Patent number
US08227507B2

Reaction notes

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