Ethyl vinyl ether → 1-iodo-3-(1-ethoxyethoxy)-3-(3-ethylcyclobutyl)-1E-propene

A mixture containing 4.8 g (0.018 mole) of 1-(3-ethylcyclobutyl)-trans-3-iodoprop-2-en-1-ol (prepared in 1I) and 38.2 g (50 ml, 0.51 mole) of ethylvinyl ether (Aldrich Chemical Company; Beilstein 1:433) was prepared. One drop of phosphorus oxychloride was added thereto and the mixture was allowed to stir for about 15 hr at room temperature. The mixture was poured into 50 ml of saturated aqueous sodium bicarbonate and the products were extracted with 150 ml (3×50 ml) of ether. The combined ether extract was washed with 50 ml of saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed in vacuo. The residue was chromatographed on silica gel 60 (0.063-0.2 mm, 70-230 mesh, ASTM) using chloroform as the eluant to yield 4.2 g of the title compound having the following physical characteristics:

1. customwas prepared
2. extractionthe products were extracted with 150 ml (3×50 ml) of ether
3. extractionThe combined ether extract
4. washwas washed with 50 ml of saturated aqueous sodium chloride
5. dry with materialdried over anhydrous magnesium sulfate
6. filtrationfiltered
7. customthe solvent was removed in vacuo
8. customThe residue was chromatographed on silica gel 60 (0.063-0.2 mm, 70-230 mesh, ASTM)

ORD record

ord-2cc08db15e074b3f9e6e95d47b719f68

Source dataset

uspto-grants-1980_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04220795