Carbon Dioxide → HCID 19041776, compound

Temperature

-78 °C

2-(3,4-dimethoxy-5-iodophenyl)-1,3-dioxane (42) (FIG. 22) (1.7 g, 4.86 mmole) was dissolved in 40 ml dry THF and cooled to -78° C. under an argon atmosphere. n-butyllithium (4.3 ml of a 1.25M soln.) was added and the reaction was warmed to 0° C. and was stirred at that temperature for an additional 45 minutes. The aryl lithium solution was then poured onto solid carbon dioxide covered with anhydrous diethyl ether. A white precipitate formed immediately. Water was added and the organic solvent subsequently removed in vacuo. The remaining aqueous solution was extracted with ethyl acetate. The organic layer was washed with 5% sodium thiosulfate, water, and then stirred vigorously over an equivolume of 10% HCl overnight. The organic layer was separated and the product extracted into 10% K2CO3. The basic solution was acidified with 10% HCl and the product extracted into chloroform. The organic layer was dried over MgSO4, and concentrated in vacuo to a white solid (0.412 g, 40%). The solid can be recrystallized from hexane/ethyl acetate.

1. addition) was added
2. temperaturethe reaction was warmed to 0° C.
3. customA white precipitate formed immediately
4. customthe organic solvent subsequently removed in vacuo
5. extractionThe remaining aqueous solution was extracted with ethyl acetate
6. washThe organic layer was washed with 5% sodium thiosulfate, water
7. stirringstirred vigorously over an equivolume of 10% HCl overnight
8. customThe organic layer was separated
9. extractionthe product extracted into 10% K2CO3
10. extractionthe product extracted into chloroform
11. dry with materialThe organic layer was dried over MgSO4
12. concentrationconcentrated in vacuo to a white solid (0.412 g, 40%)
13. customThe solid can be recrystallized from hexane/ethyl acetate

ORD record

ord-c15193003e8340f29c6e12605e724a80

Source dataset

uspto-grants-1997_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05639782