Sodium Hydroxide → HCID 66667026, compound

HRID 1628375Notes

Reaction equation

HRID 1628375 reaction equation
[CH2:1]([C:3]1([CH2:7][O:8][CH:9]=[CH2:10])[CH2:6][O:5][CH2:4]1)[CH3:2].C12CCCC(CCC1)B12[H]B2(C3CCCC2CCC3)[H]1.[C:31]1([C:62]2[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=2)[CH:36]=[CH:35][CH:34]=[C:33]([C:37]2[N:42]=[C:41]([C:43]3[CH:44]=[C:45]([C:49]4[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=4)[CH:46]=[CH:47][CH:48]=3)[N:40]=[C:39]([C:55]3[CH:60]=[CH:59][CH:58]=[C:57](Br)[CH:56]=3)[N:38]=2)[CH:32]=1.[OH-].[Na+]>C1(C)C=CC=CC=1>[C:31]1([C:62]2[CH:63]=[CH:64][CH:65]=[CH:66][CH:67]=2)[CH:36]=[CH:35][CH:34]=[C:33]([C:37]2[N:42]=[C:41]([C:43]3[CH:44]=[C:45]([C:49]4[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=4)[CH:46]=[CH:47][CH:48]=3)[N:40]=[C:39]([C:55]3[CH:56]=[CH:57][CH:58]=[C:59]([CH2:10][CH2:9][O:8][CH2:7][C:3]4([CH2:1][CH3:2])[CH2:6][O:5][CH2:4]4)[CH:60]=3)[N:38]=2)[CH:32]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 66666456HCID 66666456, compoundHCID 66666479HCID 66666479, compound

Product 1

HCID 66667026HCID 66667026, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
20 °C

Procedure

13.1 g of 3-ethyl-3-vinyloxymethyloxetane and 11.3 g of 9-BBN dimer (9-borabicyclo(3.3.1)nonane dimer) are dissolved in 200 ml of toluene at room temperature under protective gas and stirred for 20° C. During the reaction, the suspension of 9BBN slowly dissolves. 50 g of 2,4-bis-biphenyl-3-yl-6-(3-bromophenyl)-1,3,5-triazine and 50 ml of a 1M NaOH solution are subsequently added to the reaction solution. The reaction mixture is carefully degassed, and 200 mg of tetrakistriphenylphosphinepalladium are added, and the mixture is heated under reflux for 20 hours. The solution is cooled to room temperature. The phases are separated. The aqueous phase is extracted three times with toluene, the combined organic phases are subsequently washed twice with water, dried over magnesium sulfate, filtered, and the solvent is stripped off in vacuo.

Workup

  1. customDuring the reaction
  2. additionthe suspension of 9BBN
  3. dissolutionslowly dissolves
  4. customThe reaction mixture is carefully degassed
  5. addition200 mg of tetrakistriphenylphosphinepalladium are added
  6. temperaturethe mixture is heated
  7. temperatureunder reflux for 20 hours
  8. temperatureThe solution is cooled to room temperature
  9. customThe phases are separated
  10. extractionThe aqueous phase is extracted three times with toluene
  11. washthe combined organic phases are subsequently washed twice with water
  12. dry with materialdried over magnesium sulfate
  13. filtrationfiltered

Sources & evidence

ORD record
ord-ff10e413ad194a4484045755dbd07a29
Source dataset
uspto-grants-2014_07
Patent number
US08786181B2

Reaction notes

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