反応 #51263

反応方程式

n-butyllithium

tetramethylethylenediamine

diiodomethane

4,4-dimethylchroman

→

4,4-dimethyl-8-iodochroman

溶媒

ethyl ether

water

ethyl ether

反応条件

後処理

1. 1
   温度Cooling
2. 2
   その他is carried out to 0° C.
3. 3
   温度the preceding solution, cooled beforehand to −78° C.
4. 4
   workup.ADDITIONis introduced
5. 5
   その他to return to room temperature
6. 6
   workup.STIRRINGstirred for 12 hours
7. 7
   抽出extracted with ethyl ether
8. 8
   その他the organic phase is separated
9. 9
   乾燥dried over magnesium sulphate
10. 10
    その他evaporated
11. 11
    その他The residue obtained
12. 12
    その他is purified by chromatography on a silica column
13. 13
    洗浄eluted with heptane
14. 14
    その他After evaporating the solvents, 1.30 g (37%) of the expected compound
15. 15
    その他are collected in the form of a pale-yellow oil

実験手順

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.

出典