Chlorotrimethylsilane → HCID 10093926, compound

HRID 1612713Notes

Reaction equation

HRID 1612713 reaction equation
C(N(CC)CC)C.[CH2:8]([PH:12](=[O:16])[O:13][CH2:14][CH3:15])[CH2:9][CH2:10][CH3:11].[CH3:17][Si:18]([CH3:21])([CH3:20])Cl.[O:22]1[CH2:36][CH:23]1[CH2:24][N:25]1[C:29](=[O:30])[C:28]2=[CH:31][CH:32]=[CH:33][CH:34]=[C:27]2[C:26]1=[O:35]>O1CCCC1.ClCCl.[Cl-].[Zn+2].[Cl-]>[C:26]1(=[O:35])[N:25]([CH2:24][CH:23]([O:22][Si:18]([CH3:21])([CH3:20])[CH3:17])[CH2:36][P:12]([CH2:8][CH2:9][CH2:10][CH3:11])(=[O:16])[O:13][CH2:14][CH3:15])[C:29](=[O:30])[C:28]2=[CH:31][CH:32]=[CH:33][CH:34]=[C:27]12

Participants

8

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 21601N-(2,3-Epoxypropyl)phthalimideHCID 178454912HCID 178454912, compound

Product 1

HCID 10093926HCID 10093926, compound

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3.79 g of anhydrous triethylamine and 4.5 g ethyl n-butylphosphinate in 100 ml of anhydrous tetrahydrofuran under an inert atmosphere is treated with 4.07 g of trimethylchlorosilane. The resulting suspension is stirred for 20 hours at room temperature and the solid removed by filtration. Concentration in vacuo affords a cloudy, colourless oil which is treated with 6.09 g of anhydrous N-(2,3-epoxypropyl)phthalimide and 0.5 g of anhydrous zinc chloride. The mixture is heated to 66° C. under an inert atmosphere for 3 hours, cooled to 20° and diluted with dichloromethane. The organic solution is washed with 100 ml 10% of aqueous sodium bicarbonate solution and dried over anhydrous magnesium sulphate. Removal of the solvent and chromatography on silica gel affords ethyl 3-phthalimido-2-trimethylsilyloxy-propyl(n-butyl)phosphinate as a viscous oil.

Workup

  1. customthe solid removed by filtration
  2. concentrationConcentration in vacuo
  3. customaffords a cloudy, colourless oil which
  4. temperatureThe mixture is heated to 66° C. under an inert atmosphere for 3 hours
  5. temperaturecooled to 20°
  6. washThe organic solution is washed with 100 ml 10% of aqueous sodium bicarbonate solution
  7. dry with materialdried over anhydrous magnesium sulphate
  8. customRemoval of the solvent and chromatography on silica gel

Sources & evidence

ORD record
ord-66c1e51faca44193ba98be06c8b307d4
Source dataset
uspto-grants-1993_03
Patent number
US05190933

Reaction notes

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