Diethyl Ether → Triphenyl-(5-trimethylsilylpent-4-inyl)phosphonium iodide

HRID 2064515Notes

Reaction equation

[CH2:1]([Si:3]([CH2:12]C)([CH2:10]C)[C:4]#[C:5][CH2:6][CH2:7][CH2:8][I:9])C.[C:14]1([P:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(OCC)C>C(O)C>[I-:9].[C:27]1([P+:20]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:8][CH2:7][CH2:6][C:5]#[C:4][Si:3]([CH3:1])([CH3:10])[CH3:12])[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of triethyl-(5-iodpent-1-inyl)silane (5.02 g, 16.3 mmol) and triphenylphosphine (3.94 g, 15 mmol) in absolute ethanol (100 mL) was stirred 4 h with reflux and overnight at 50° C. and then heated once again with reflux for 7 h. The reaction solution was then concentrated to low volume in a vacuum, the yellowish crystals formed were mixed with diethyl ether (50 mL) and stirred. The diethyl ether was itself concentrated to low volume in a vacuum and the crystals mixed with ethyl acetate (50 mL). After standing in the refrigerator for 24 h the crystals were aspirated, washed with cold ethyl acetate (50 mL) and dried in an exsiccator over phosphorus pentoxide.

Workup

temperatureheated once again
temperaturewith reflux for 7 h
concentrationThe reaction solution was then concentrated to low volume in a vacuum
customthe yellowish crystals formed
concentrationconcentrated to low volume in a vacuum
additionthe crystals mixed with ethyl acetate (50 mL)
washwashed with cold ethyl acetate (50 mL)
dry with materialdried in an exsiccator over phosphorus pentoxide

Sources & evidence

ORD record: ord-0d0d0276ae7b4f1b917d12792ebaaace
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08288430B2

Reaction notes

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