反応 #71081

反応方程式

N2

1-[4-(tert-butyl-dimethyl-silanyloxymethyl)-pyridin-2-yl]-ethanone

ethylene glycol

trimethylorthoformate

→

title compound

4-(tert-Butyl-dimethyl-silanyloxymethyl)-2-(2-methyl-[1,3]dioxolan-2-yl)-pyridine

溶媒

NaHCO3

反応条件

後処理

1. 1
   その他In a flame dried round-bottomed flask equipped with a magnetic stir bar
2. 2
   抽出the mixture was extracted with EA (50 mL)
3. 3
   洗浄extracts were washed with brine (2×50 mL)
4. 4
   乾燥dried over MgSO4
5. 5
   ろ過filtered
6. 6
   その他the solvent was removed under reduced pressure
7. 7
   その他Purification of the residue by FC (20:1 to 1:1 hept-EA)

実験手順

In a flame dried round-bottomed flask equipped with a magnetic stir bar and a Dean-Stark apparatus under inert atmosphere (N2), a solution of 1-[4-(tert-butyl-dimethyl-silanyloxymethyl)-pyridin-2-yl]-ethanone (1.78 g, 6.71 mmol) in ethylene glycol (7.14 mL, 127.95 mmol) was treated with trimethylorthoformate (1.50 mL, 13.67 mmol) followed by LiBF4 (128 mg, 1.34 mmol). The reaction mixture was heated at 95° C. overnight. Sat. aq. NaHCO3 (50 mL) was added and the mixture was extracted with EA (50 mL). The org. extracts were washed with brine (2×50 mL), dried over MgSO4, filtered, and the solvent was removed under reduced pressure. Purification of the residue by FC (20:1 to 1:1 hept-EA) gave the title compound as a yellow oil. TLC:rf (1:1 hept-EA)=0.50. LC-MS-conditions 02: tR=0.91 min, [M+H]+=310.40.

出典