反応 #71082

反応方程式

N2

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

TBAF

→

title compound

[2-(2-Methyl-[1,3]dioxolan-2-yl)-pyridin-4-yl]-methanol

溶媒

EA

THF

THF

反応条件

後処理

1. 1
   洗浄washed with brine (3×10 mL)
2. 2
   乾燥dried over MgSO4
3. 3
   ろ過filtered
4. 4
   濃縮concentrated under reduced pressure
5. 5
   その他Purification of the residue by FC (5:1 to 1:3 hept-EA)

実験手順

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 4-(tert-butyl-dimethyl-silanyloxymethyl)-2-(2-methyl-[1,3]dioxolan-2-yl)-pyridine (840 mg, 2.71 mmol) in dry THF (15 mL) was treated at 0° C. with TBAF (4.70 mL of a 1M solution in THF, 4.70 mmol). The reaction mixture was stirred at 0° C. for 5 min and at rt for 1.5 h. The mixture was then diluted with EA (10 mL), washed with brine (3×10 mL), dried over MgSO4, filtered and concentrated under reduced pressure. Purification of the residue by FC (5:1 to 1:3 hept-EA) gave the title compound as a yellow oil. TLC:rf (1:2 hept-EA)=0.10. LC-MS-conditions 02: tR=0.33 min; [M+H]+=196.54.

出典