反応 #508760

反応方程式

Trans-cinnamic acid

tetrabutylammonium hydroxide

2-(trimethylsilyl)ethyl 2-(tert-butyl((chloromethoxy)carbonyl)amino)-acetate

→

4-tert-butyl-10,10-dimethyl-3,6-dioxo-2,7-dioxa-4-aza-10-silaundec-1-yl (2E)-3-phenylacrylate

溶媒

methanol

反応条件

後処理

1. 1
   その他the methanol is removed
2. 2
   workup.ADDITIONTHF is added
3. 3
   その他The solvent is removed
4. 4
   workup.ADDITIONthe residue is diluted with ether
5. 5
   洗浄The resulting solution is washed with water and brine
6. 6
   乾燥The organic layer is dried over magnesium sulfate
7. 7
   ろ過filtered
8. 8
   濃縮concentrated under reduced pressure
9. 9
   その他to yield 5.01 g (61%)

実験手順

Trans-cinnamic acid (23.1 mmol) and 1.0 M tetrabutylammonium hydroxide (22.2 mmol) in methanol are stirred for one hour, and the methanol is removed. THF is added. To this solution is added 2-(trimethylsilyl)ethyl 2-(tert-butyl((chloromethoxy)carbonyl)amino)-acetate (18.5 mmol) and the mixture is stirred at room temperature for 24 hr. The solvent is removed and the residue is diluted with ether. The resulting solution is washed with water and brine. The organic layer is dried over magnesium sulfate, filtered and concentrated under reduced pressure to yield 5.01 g (61%) MS (ESI) m/z 436.3.

出典