Diiodomethane → 4,4-Dimethyl-8-iodochroman

Temperature

-78 °C

2.00 g (12.3 mmol) of 4,4-dimethylchroman and 30 ml of ethyl ether are introduced into a three-necked flask under argon. 2.4 m (15.9 mmol) of tetramethylethylenediamine (TMEDA) are added dropwise, the mixture is cooled to −78° C. and 5.9 ml (14.8 mmol) of n-butyllithium (2.5M in hexane) are added dropwise. The temperature is allowed to return to −20 °C. over two hours and then to room temperature and the mixture is stirred for 12 hours. 1.3 ml (16.0 mmol) of diiodomethane and 15 ml of ethyl ether are introduced into another three-necked flask under argon. Cooling is carried out to 0° C. and the preceding solution, cooled beforehand to −78° C., is introduced, then the reaction mixture is allowed to return to room temperature and stirred for 12 hours. The reaction mixture is poured into water and extracted with ethyl ether and the organic phase is separated by settling, dried over magnesium sulphate and evaporated. The residue obtained is purified by chromatography on a silica column eluted with heptane. After evaporating the solvents, 1.30 g (37%) of the expected compound are collected in the form of a pale-yellow oil.

1. temperatureCooling
2. customis carried out to 0° C.
3. temperaturethe preceding solution, cooled beforehand to −78° C.
4. additionis introduced
5. customto return to room temperature
6. stirringstirred for 12 hours
7. extractionextracted with ethyl ether
8. customthe organic phase is separated
9. dry with materialdried over magnesium sulphate
10. customevaporated
11. customThe residue obtained
12. customis purified by chromatography on a silica column
13. washeluted with heptane
14. customAfter evaporating the solvents, 1.30 g (37%) of the expected compound
15. customare collected in the form of a pale-yellow oil

ORD record

ord-ff08d95129cc44a389739f198e52c21d

Source dataset

uspto-grants-2005_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06849658B2