Sodium Carbonate → Triphenyl-(tris(trimethylsiloxy)silylpropyl)phosphonium iodide

HRID 1478942Notes

Reaction equation

HRID 1478942 reaction equation
[I:1][CH2:2][CH2:3][CH2:4][Si:5]([O:16][Si:17]([CH3:20])([CH3:19])[CH3:18])([O:11][Si:12]([CH3:15])([CH3:14])[CH3:13])[O:6][Si:7]([CH3:10])([CH3:9])[CH3:8].[C:21]1([P:27]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1>[I-:1].[C:34]1([P+:27]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:2][CH2:3][CH2:4][Si:5]([O:16][Si:17]([CH3:20])([CH3:19])[CH3:18])([O:11][Si:12]([CH3:15])([CH3:14])[CH3:13])[O:6][Si:7]([CH3:10])([CH3:9])[CH3:8])[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 223256933-Iodopropyl-tris(trimethylsiloxy)silane

Product 1

HCID 87426320Triphenyl-(tris(trimethylsiloxy)silylpropyl)phosphonium iodide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.0 g of 3-iodopropyltris(trimethylsiloxy)silane (28) described in Step 6.1, 1.7 g of triphenylphosphine and 0.69 g of sodium carbonate are added to 50 ml of tetrahydrofurane. The reaction mixture is stirred for 2 days at reflux. The solvent is evaporated and the residue purified by column chromatography on silica gel to give the desired phosphonium salt (37); ESI-MS: M+599.58.

Workup

  1. temperatureat reflux
  2. customThe solvent is evaporated
  3. customthe residue purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-b626b74765b84d35a41aaeb7b64376e0
Source dataset
uspto-grants-2016_08
Patent number
US09403987B2

Reaction notes

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