Triethylamine → HCID 67026219, compound

HRID 2410631Notes

Reaction equation

HRID 2410631 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[PH:9](=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:16][CH3:17])[CH3:2].C(N(CC)CC)C.Cl[SiH](Cl)Cl>C(#N)C>[CH2:16]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[PH:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[CH2:1][CH3:2])[CH3:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24811Trichlorosilane2×HCID 178436119HCID 178436119, compound

Product 1

HCID 67026219HCID 67026219, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Into a 1 L Schlenk flask was added the phosphine oxide (3a) (17.21 g, 66.7 mmol). To this was added acetonitrile (400 ml) and triethylamine (27.9 ml, 200.1 mmol). Then trichlorosilane (20.2 ml, 200.1 mmol) was added slowly. The addition of the trichlorosilane gave the formation of some white precipitate. The resultant mixture was then refluxed overnight. The resultant suspension was then cooled to 0° in an ice bath and a solution of potassium hydroxide (40 g) in water (200 ml) which had been degassed with nitrogen gas was added slowly. This gave a bi-phasic mixture. Additional acetonitrile (100 ml) was then added. The upper organic phase was then removed by cannula into a clean Schlenk flask and the solvent removed under vacuum. This gave an off-white solid (3b). Yield=13.60 g, 84%.

Workup

  1. customgave the formation of some white precipitate
  2. customa solution of potassium hydroxide (40 g) in water (200 ml) which had been degassed with nitrogen gas
  3. additionwas added slowly
  4. customThis gave a bi-phasic mixture
  5. customThe upper organic phase was then removed by cannula into a clean Schlenk flask
  6. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-6b9c7178c1914d43bf34cb4369b74eba
Source dataset
uspto-grants-2014_08
Patent number
US08816113B2

Reaction notes

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