Triethylamine → HCID 15831604, compound

HRID 1452996Notes

Reaction equation

HRID 1452996 reaction equation
[C:1]1([P:7]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)([C:9]2[CH:36]=[CH:35][CH:34]=[CH:33][C:10]=2[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2P(C2C=CC=CC=2)(C2C=CC=CC=2)=O)=[O:12])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.Cl[SiH](Cl)Cl.[OH-].[Na+]>CCCCCC.C1(C)C=CC=CC=1>[C:1]1([P:7]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:9]2[CH:36]=[CH:35][CH:34]=[CH:33][C:10]=2[CH:11]([OH:12])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 24811TrichlorosilaneHCID 23124062HCID 23124062, compound

Product 1

HCID 15831604HCID 15831604, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Procedure

Into 10 ml of toluene was dissolved 252 mg (0.36 mmol) of 2,2′-bis{diphenylphosphinyl}benzophenone, and further 2.0 ml (14.4 mmol) of triethylamine was added thereto. 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 added dropwise 10 ml of 25% aqueous sodium hydroxide slowly. The aqueous phase was extracted with 10 ml of methylene chloride. The organic phases were combined, and the resultant was 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. washthe resultant was washed 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

Sources & evidence

ORD record
ord-e63b981b7f764e6084a75b18d17c4693
Source dataset
uspto-grants-2009_01
Patent number
US07473793B2

Reaction notes

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