Triethylamine → HCID 16082226, compound

HRID 1452997Notes

Reaction equation

HRID 1452997 reaction equation
[C:1]1([P:9]([C:43]2[CH:48]=[C:47]([CH3:49])[CH:46]=[C:45]([CH3:50])[CH:44]=2)([C:11]2[CH:42]=[CH:41][CH:40]=[CH:39][C:12]=2[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[P:21]([C:31]2[CH:36]=[C:35]([CH3:37])[CH:34]=[C:33]([CH3:38])[CH:32]=2)([C:23]2[CH:28]=[C:27]([CH3:29])[CH:26]=[C:25]([CH3:30])[CH:24]=2)=O)=[O:14])=O)[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[CH:2]=1.C(N(CC)CC)C.Cl[SiH](Cl)Cl.[OH-].[Na+]>C1(C)C=CC=CC=1>[C:31]1([P:21]([C:23]2[CH:24]=[C:25]([CH3:30])[CH:26]=[C:27]([CH3:29])[CH:28]=2)[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[C:13]([C:12]2[CH:39]=[CH:40][CH:41]=[CH:42][C:11]=2[P:9]([C:1]2[CH:2]=[C:3]([CH3:8])[CH:4]=[C:5]([CH3:7])[CH:6]=2)[C:43]2[CH:48]=[C:47]([CH3:49])[CH:46]=[C:45]([CH3:50])[CH:44]=2)=[O:14])[CH:36]=[C:35]([CH3:37])[CH:34]=[C:33]([CH3:38])[CH:32]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 24811TrichlorosilaneHCID 23124065HCID 23124065, compound

Product 1

HCID 16082226HCID 16082226, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Into 10 ml of toluene was dissolved 252 mg (0.36 mmol) of 2,2′-bis{di-(3,5-xylyl)phosphinyl}benzophenone, and further 2.0 ml (14.4 mmol) of triethylamine was added thereto, and the resultant solution was cooled to 0° C. Thereto was added 360 μl (3.6 mmol) of trichlorosilane, and then the resultant solution was stirred for 30 minutes while the temperature thereof was kept at 0° C. Thereafter, the temperature thereof was slowly raised to a temperature at which the solution was allowed to be refluxed. The solution was then refluxed for 4 hours. The reaction mixture was cooled, and thereto was dropwise added 10 ml of 25% aqueous sodium hydroxide slowly. The aqueous phase was extracted with 10 ml of methylene chloride. The organic phases were combined, washed with 1N hydrochloric acid two times and then dried over magnesium sulfate. The resultant was concentrated under reduced pressure to distill off the solvent, and then purified by column chromatography on silica gel (ethyl acetate:hexane=1:6) to give 47.7 mg (yield: 20%) of the title compound in the form of a yellow solid.

Workup

  1. additionwas added
  2. customthereof was kept at 0° C
  3. temperatureThereafter, the temperature thereof was slowly raised to a temperature at which the solution
  4. temperatureto be refluxed
  5. temperatureThe solution was then refluxed for 4 hours
  6. temperatureThe reaction mixture was cooled
  7. extractionThe aqueous phase was extracted with 10 ml of methylene chloride
  8. washwashed with 1N hydrochloric acid two times
  9. dry with materialdried over magnesium sulfate
  10. concentrationThe resultant was concentrated under reduced pressure
  11. distillationto distill off the solvent
  12. custompurified by column chromatography on silica gel (ethyl acetate:hexane=1:6)

Sources & evidence

ORD record
ord-511245370dbe4e56894be0f39f01f951
Source dataset
uspto-grants-2009_01
Patent number
US07473793B2

Reaction notes

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