Sodium Iodide → HCID 12235558, compound

HRID 2380712Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].[OH:9][C:10]1[CH:22]=[CH:21][C:13](/[CH:14]=[CH:15]/[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:12][CH:11]=1.[CH2:23](Br)[CH:24]([CH3:26])[CH3:25]>CS(C)=O.O>[CH2:23]([O:9][C:10]1[CH:11]=[CH:12][C:13](/[CH:14]=[CH:15]/[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:21][CH:22]=1)[CH:24]([CH3:26])[CH3:25]

Participants

Conditions

Temperature: 60 °C

Procedure

13.8 g of potassium carbonate and 7.50 g of sodium iodide were added to a solution of 9.61 g of ethyl (E)-p-hydroxycinnamate and 8.22 g of isobutylbromide in 100 ml of dimethyl sulfoxide. The reaction mixture was then stirred for 20 hours at 60° C., after which it was cooled to the room temperature. The reaction mixture was then poured into 1 liter of water and extracted twice with ethyl acetate. The combined extracts were washed with water and dried over anhydrous sodium sulfate; the solvent was then removed by evaporation under reduced pressure. The residue was purified by flash column chromatography using 300 g of silica gel, eluted with a 5:1 by volume solution of hexane and ethyl acetate, to give 10.71 g of the title compound as a colorless oil (which solidified at low temperature).

Workup

temperatureafter which it was cooled to the room temperature
extractionextracted twice with ethyl acetate
washThe combined extracts were washed with water
dry with materialdried over anhydrous sodium sulfate
customthe solvent was then removed by evaporation under reduced pressure
customThe residue was purified by flash column chromatography
washeluted with a 5:1 by volume solution of hexane and ethyl acetate

Sources & evidence

ORD record: ord-eec97eb4cee24e29a63c662bc229db30
Source dataset: uspto-grants-1994_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05369106

Reaction notes

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