Potassium Carbonate → 2-(2,4,6-Triiodophenoxy)ethylcyclopentane

HRID 53491Notes

Reaction equation

[I:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[C:4]([I:9])[C:3]=1[OH:10].C(=O)([O-])[O-].[K+].[K+].[CH:17]1([CH2:22][CH2:23]CS([O-])(=O)=O)[CH2:21][CH2:20][CH2:19][CH2:18]1>CN(C)C=O>[I:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[C:4]([I:9])[C:3]=1[O:10][CH2:23][CH2:22][CH:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

Conditions

Temperature: 65 °C

Procedure

To a stirred mixture of 2,4,6-triiodophenol (20.36 g, 43.2 mmol) and milled anhydrous potassium carbonate (7.2 g, 52.2 mmol) in 75 ml of dry dimethylformamide was added dropwise over 10 minutes, a solution of 2-cyclopentylethylmethanesulfonate (8.2 g, 42.7 mmol) in 10 ml of dimethylformamide. The mixture was heated at 65° C. under argon overnight and the solvent was then removed under vacuum. The resulting amber residue was partitioned between ethyl acetate (200 ml) and water (30 ml). The aqueous layer was further extracted with ethyl acetate (2×250 ml) and the combined ethyl acetate extracts were treated with decolorizing carbon, dried over magnesium sulfate and passed through a short pad of basic alumina. The filtrate was evaporated under vacuum to give 17.5 g (73%) of the desired product as an amber oil.

Workup

additionwas added dropwise over 10 minutes
customthe solvent was then removed under vacuum
customThe resulting amber residue was partitioned between ethyl acetate (200 ml) and water (30 ml)
extractionThe aqueous layer was further extracted with ethyl acetate (2×250 ml)
additionthe combined ethyl acetate extracts were treated with decolorizing carbon
dry with materialdried over magnesium sulfate
customThe filtrate was evaporated under vacuum

Sources & evidence

ORD record: ord-1c3727e7675b4534be0082caf2972479
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05620677

Reaction notes

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