Chlorotrimethylsilane → Ethyl 3-phthalimido-2-trimethylsilyloxy-propyl(ethyl)phosphinate

HRID 1612707Notes

Reaction equation

HRID 1612707 reaction equation
C(N(CC)CC)C.[CH2:8]([PH:10](=[O:14])[O:11][CH2:12][CH3:13])[CH3:9].Cl[Si:16]([CH3:19])([CH3:18])[CH3:17].[O:20]1[CH2:34][CH:21]1[CH2:22][N:23]1[C:27](=[O:28])[C:26]2=[CH:29][CH:30]=[CH:31][CH:32]=[C:25]2[C:24]1=[O:33]>O1CCCC1.ClCCl.[Cl-].[Zn+2].[Cl-]>[C:27]1(=[O:28])[N:23]([CH2:22][CH:21]([O:20][Si:16]([CH3:19])([CH3:18])[CH3:17])[CH2:34][P:10]([CH2:8][CH3:9])(=[O:14])[O:11][CH2:12][CH3:13])[C:24](=[O:33])[C:25]2=[CH:32][CH:31]=[CH:30][CH:29]=[C:26]12

Participants

8

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 21601N-(2,3-Epoxypropyl)phthalimideHCID 178476785HCID 178476785, compound

Product 1

HCID 19090885Ethyl 3-phthalimido-2-trimethylsilyloxy-propyl(ethyl)phosphinate

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4.55 g of anhydrous triethylamine and 5.0 g of ethyl ethylphosphinate in 100 ml of anhydrous tetrahydrofuran under an inert atmosphere is treated with 4.89 g of chlorotrimethylsilane. 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 5.10 g of anhydrous N-(2,3-epoxypropyl)phthalimide and 1.0 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 of a 10% aqueous sodium bicarbonate solution and dried over anhydrous magnesium sulphate. Removal of the solvents and chromatography on silica gel affords ethyl 3-phthalimido-2-trimethylsilyloxy-propyl(ethyl)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 of a 10% aqueous sodium bicarbonate solution
  7. dry with materialdried over anhydrous magnesium sulphate
  8. customRemoval of the solvents and chromatography on silica gel

Sources & evidence

ORD record
ord-3b8ddaf588314906b0813c40427d48fa
Source dataset
uspto-grants-1993_03
Patent number
US05190933

Reaction notes

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