تفاعل #660885

معادلة التفاعل

(S)-5-(tert-butyldimethylsilyloxy)-4-iodo-2-isopropyl-7,7-dimethyl-5,6,7,8-tetrahydroquinoline-3-carbaldehyde

isopropylmagnesium chloride

4-iodobenzotrifluoride

methanol

→

(S)—((S)-5-(tert-butyldimethylsilyloxy)-4-iodo-2-isopropyl-7,7-dimethyl-5,6,7,8-tetrahydroquinolin-3-yl)(4-(trifluoromethyl)phenyl)methanol

المذيبات

tetrahydrofurane

tetrahydrofurane

tetrahydrofurane

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThen the solution is cooled to −40° C.
2. 2
   workup.STIRRINGThe mixture is stirred for 12 hours
3. 3
   درجة الحرارةwhile warming to room temperature
4. 4
   درجة الحرارةThen it is cooled to 0° C.
5. 5
   workup.STIRRINGit is stirred for 30 minutes
6. 6
   أخرىThe solvents are evaporated in vacuo
7. 7
   أخرىthe residue is chromatographed on silica gel (cyclohexane/ethylacetate 95:5 to 80:20)

الإجراء التجريبي

1.1 ml 4-iodobenzotrifluoride are dissolved in 60 ml tetrahydrofurane and cooled to −20° C. 3.7 ml of a 2 M solution of isopropylmagnesium chloride in tetrahydrofurane are added dropwise and the solution is stirred for further 5 hours. Then the solution is cooled to −40° C. and 1.17 g (S)-5-(tert-butyldimethylsilyloxy)-4-iodo-2-isopropyl-7,7-dimethyl-5,6,7,8-tetrahydroquinoline-3-carbaldehyde in 5 ml tetrahydrofurane are added dropwise. The mixture is stirred for 12 hours while warming to room temperature. Then it is cooled to 0° C., 10 ml methanol are added and it is stirred for 30 minutes. The solvents are evaporated in vacuo and the residue is chromatographed on silica gel (cyclohexane/ethylacetate 95:5 to 80:20).

المصدر