Chlorotrimethylsilane → 6-(2-Iodophenyl)-3-hexanone

Temperature

-78 °C

Lithium chloride (6.6 g, 150 mmole) (dried overnight at 115° C. under vacuum) and copper(I) cyanide (6.72 g, 75 mmole) were stirred with tetrahydrofuran (75 ml) under nitrogen for 10 minutes then cooled to −78° C. A solution of 2-iodobenzyl zinc bromide (150 ml, 0.5M in THF, 75 mmol) was added and the mixture was warmed to −15° C., held at this temperature for 20 min then re-cooled to −78° C. Chlorotrimethylsilane (19.1 ml, 150 mmol) was added followed by a solution of ethyl vinyl ketone (7.4 ml, 74.3 mmol) in tetrahydrofuran (15 ml). The mixture was stirred at −78° C. for 3 hours then warmed to room temperature and stirred for 1 hour before being poured into a mixture of water (400 ml) and ether (400 ml). The aqueous layer was extracted with ether (2×400 ml) and the combined ethereal solutions were washed with brine (2×200 ml), dried over anhydrous magnesium sulphate and evaporated in vacuo to give the title compound as a pale yellow liquid (23 g).

1. temperaturethe mixture was warmed to −15° C.
2. temperaturethen re-cooled to −78° C
3. temperaturethen warmed to room temperature
4. stirringstirred for 1 hour
5. extractionThe aqueous layer was extracted with ether (2×400 ml)
6. washthe combined ethereal solutions were washed with brine (2×200 ml)
7. dry with materialdried over anhydrous magnesium sulphate
8. customevaporated in vacuo

ORD record

ord-4a1f48bb7bd44adaa8be894b7b78b62d

Source dataset

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07902224B2